Triethylamine → Z-Phe-gly-NH2

HRID 1368805Notes

Reaction equation

HRID 1368805 reaction equation
[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:2]([C:10]([O:12]CC1C=CC=CC=1)=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[NH2:31][CH2:32][C:33]([NH2:35])=[O:34].CCN(CC)CC>CN(C=O)C.O.CCOC(C)=O>[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[C@H:2]([C:10]([NH:31][CH2:32][C:33]([NH2:35])=[O:34])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 2723639Glycinamide hydrochlorideHCID 7016068Z-Phe-OBzl

Product 1

HCID 7020269Z-Phe-gly-NH2Yield 100.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Z-L-Phe-OBn (25, 19.2 mg, 0.05 mmol) in DMF (0.25 mL) and water (0.144 mL), glycinamide hydrochloride (31, 17 mg, 0.15 mmol) and Et3N (0.15 mmol, 0.0625 mL) were added, followed by the addition of S166C—S-inden-oxaz(S,R) (ME-n, 0.106 mL, 0.5 mg of active enzyme in 10 mM MES buffer (pH 5.8) including 1 mM CaCl2). The reaction was stirred for one hour at room temperature. The mixture was diluted with AcOEt and washed with 1 M KHSO4 (1 mL×1) and brine (1 mL×1), and the organic layer was dried over MgSO4. After evaporation, the residue was purified by preparative TLC (CH2Cl2/MeOH=90/10) to afford Z-L-Phe-Gly-NH2 (33, 17.8 mg, quantitative).

Workup

  1. washwashed with 1 M KHSO4 (1 mL×1) and brine (1 mL×1)
  2. dry with materialthe organic layer was dried over MgSO4
  3. customAfter evaporation
  4. customthe residue was purified by preparative TLC (CH2Cl2/MeOH=90/10)

Sources & evidence

ORD record
ord-4918a73439e448c794f52932290e1d86
Source dataset
uspto-grants-2003_06
Patent number
US06576454B2

Reaction notes

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