Triethylamine → HCID 11443343, compound

HRID 1064222Notes

Reaction equation

HRID 1064222 reaction equation
[NH2:1][CH:2]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1)[CH:3]([OH:6])[CH2:4][OH:5].C(N(CC)CC)C.C1C(=O)N([O:37][C:38]([CH2:40][NH:41][C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])=O)C(=O)C1>CN(C=O)C>[CH2:45]([O:44][C:42](=[O:43])[NH:41][CH2:40][C:38](=[O:37])[NH:1][CH:2]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1)[CH:3]([OH:6])[CH2:4][OH:5])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76177Z-Gly-OSuHCID 11438165HCID 11438165, compound

Product 1

HCID 11443343HCID 11443343, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-4-(3-benzyloxy-5-fluoro-phenyl)-butane-1,2-diol (5.60 g, 18.34 mmol, 1.00 eq.), triethylamine (5.11 mL, 36.68 mmol, 2.00 eq.) and anhydrous DMF (100 mL) at 0° C. is added Z-glycine N-succinimidyl ester (6.18 g, 20.17 mmol, 1.10 eq.) with stirring under N2. After 2 hours, the reaction is quenched with 1N HCl, extracted with ethyl acetate, and washed with 10% NaHCO3 and then brine. The organic layer is then dried with MgSO4, filtered through Celite, and concentrated in vacuo, yielding the crude product as a light amber oil. Purification via flash chromatography in 5% MeOH/CHCl3 (rf. 0.33, KMnO4 stain), affords the final product as a white solid (5.40 g., 59% yield overall). Calculate mass for C27H29FN2O6: 496.20. Mass found for C27H29FN2O6: (OAMS) ES+: 497.5 (M+1).

Workup

  1. customthe reaction is quenched with 1N HCl
  2. extractionextracted with ethyl acetate
  3. washwashed with 10% NaHCO3
  4. dry with materialThe organic layer is then dried with MgSO4
  5. filtrationfiltered through Celite
  6. concentrationconcentrated in vacuo
  7. customyielding the crude product as a light amber oil
  8. customPurification via flash chromatography in 5% MeOH/CHCl3 (rf. 0.33, KMnO4 stain)

Sources & evidence

ORD record
ord-4330ea502c1b4578b57732fcad95ef47
Source dataset
uspto-grants-2005_11
Patent number
US06969709B2

Reaction notes

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