Ethanolamine → HCID 15929376, compound

HRID 1611642Notes

Reaction equation

HRID 1611642 reaction equation
[C:1]([NH:8][C@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:38]([CH2:40][NH2:41])[OH:39]>CN(C=O)C.C(Cl)(Cl)Cl.C(Cl)Cl.CO.CC(O)=O.C(Cl)Cl.CO>[C:1]([NH:8][C@H:9]([C:12]([NH:41][CH2:40][CH2:38][OH:39])=[O:14])[CH2:10][OH:11])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

9

Reactant 4

HCID 700EthanolamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 15929376HCID 15929376, compound

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolventHCID 21877243DCM MeOH AcOHSolvent

Conditions

Temperature
0 °C

Procedure

A solution comprising 6.15 g (30 mmol) of N-Boc-L-serine (1, Fluka) and 3.45 g of N-hydroxysuccinimide (30 mmol) in 80 ml of DMF is stirred at 0° C. and 6.2 g (30 mmol) of DCC are added. The reaction mixture is maintained at 0° C. for 15 min, then it is allowed to return to ambient temperature and stirring is continued for 1 h 30. 2.75 ml (60 mmol) of ethanolamine are subsequently added. After stirring for 12 h, the DCU formed is filtered off and washed with 2×15 ml of DMF. The combined organic phases are evaporated to dryness under vacuum. The product is isolated from the residual paste by flash chromatography on a silica gel column (Kieselgel Merck 60, 230-400 mesh; eluent: CH2Cl2/MeOH 6%). The expected compound is collected in the form of a gum which crystallizes from an AcOEt/hexane mixture to provide 5.21 g (Yd=70%) of colorless needles. Rf (CH2Cl2/MeOH, 9.3/0.7): 0.23; (CH2Cl2/MeOH/AcOH, 9/0.9/0.1): 0.47. M.p.=74-76° C. [α]D20=−2.2° (c 0.9, CHCl3).

Workup

  1. temperatureThe reaction mixture is maintained at 0° C. for 15 min
  2. customto return to ambient temperature
  3. stirringstirring
  4. stirringAfter stirring for 12 h
  5. customthe DCU formed
  6. filtrationis filtered off
  7. washwashed with 2×15 ml of DMF
  8. customThe combined organic phases are evaporated to dryness under vacuum
  9. customThe product is isolated from the residual paste by flash chromatography on a silica gel column (Kieselgel Merck 60, 230-400 mesh; eluent: CH2Cl2/MeOH 6%)
  10. customThe expected compound is collected in the form of a gum which
  11. customcrystallizes from an AcOEt/hexane mixture
  12. customto provide 5.21 g (Yd=70%) of colorless needles

Sources & evidence

ORD record
ord-b5600275baee404e97628badc5fea70f
Source dataset
uspto-grants-2006_01
Patent number
US06989372B1

Reaction notes

Loading…