Methanesulfonic Acid → HCID 86657361, compound

HRID 476350Notes

Reaction equation

HRID 476350 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:28][N:29]1[C:33](=[O:34])[CH2:32][CH2:31][C:30]1=[O:35].C1([N:42]=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C.[CH:58]1[CH:63]=[CH:62][C:61]([CH2:64][O:65][C:66]([C@@H:68](N)[CH2:69][CH2:70][C:71]([OH:73])=O)=[O:67])=[CH:60][CH:59]=1.CS(O)(=O)=O>CC(C)=O>[O:35]=[C:30]1[CH2:31][CH2:32][C:33](=[O:34])[N:29]1[O:28][C:71](=[O:73])[C@@H:70]([NH:42][C:24](=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:27])[CH2:69][CH2:68][C:66]([O:65][CH2:64][C:61]1[CH:62]=[CH:63][CH:58]=[CH:59][CH:60]=1)=[O:67]

Participants

8

Reactant 6

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 10868Dicyclohexylcarbodiimide2×HCID 80170N-HydroxysuccinimideHCID 7009632L-Glutamic acid alpha-benzyl esterHCID 5427134516-(Benzyloxy)-16-oxohexadecanoic acid

Product 1

HCID 86657361HCID 86657361, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

1,16-hexadecanedioic acid mono benzyl ester (20.0 g, 53.1 mmol) was dissolved in acetone at 35-40° C. N-Hydroxysuccinimide (6.42 g, 55.8 mmol) was added. To the resulting solution dicyclohexylcarbodiimide (DCC) (12.1 g, 58.4 mmol) was added. The reaction mixture was stirred for 3-4 hours at 35° C. To the resulting suspension triethylamine (7.40 ml, 53.1 mmol) and L-glutamic acid α-benzyl ester (12.6 g/53.1 mmol) were added. The reaction mixture was stirred for 8-16 hours at 35-40° C. The reaction mixture was cooled to 20-25° C. Methanesulfonic acid (3.45 ml, 53.1 mmol) and DCC (12.1 g, 53.1 mmol) were added. The reaction mixture was stirred for 8-16 hours at 20-25° C. The reaction mixture was filtered, and the filtrate evacuated to dryness. The residue was partitioned between water (100 ml) and toluene (200 ml). The toluene phase was dried by distilling off water. Silica gel (20 g) was added to the residue. The suspension was stirred for 30 minutes at 20-25° C., subsequently filtered. The volume of the filtrate was reduced to app. 100-120 ml by evaporation under reduced pressure. N-heptane (150 ml) was added over a period of 15-30 minutes. The resulting suspension was stirred for 2 hours. The product was isolated by filtration, and dried to constant weight under reduced pressure at 20-25° C. Yield 21 g (58%) of white material.

Workup

  1. stirringThe reaction mixture was stirred for 8-16 hours at 35-40° C
  2. temperatureThe reaction mixture was cooled to 20-25° C
  3. stirringThe reaction mixture was stirred for 8-16 hours at 20-25° C
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evacuated to dryness
  6. customThe residue was partitioned between water (100 ml) and toluene (200 ml)
  7. dry with materialThe toluene phase was dried
  8. distillationby distilling off water
  9. additionSilica gel (20 g) was added to the residue
  10. stirringThe suspension was stirred for 30 minutes at 20-25° C.
  11. filtrationsubsequently filtered
  12. custom100-120 ml by evaporation under reduced pressure
  13. additionN-heptane (150 ml) was added over a period of 15-30 minutes
  14. stirringThe resulting suspension was stirred for 2 hours
  15. customThe product was isolated by filtration
  16. customdried to constant weight under reduced pressure at 20-25° C

Sources & evidence

ORD record
ord-0de47a50efbb4025953c6000339ee703
Source dataset
uspto-grants-2014_01
Patent number
US08637647B2

Reaction notes

Loading…