Diisopropylethylamine → HCID 68802560, compound

HRID 2222991Notes

Reaction equation

HRID 2222991 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:15])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[C:16]([O:20][C:21]([N:23](C1C=CC=CC=1)[CH2:24][C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C.N1(OC(N(C)C)=[N+](C)C)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH2:2]([O:4][C:5](=[O:15])[C@@H:6]([NH:7][C:25](=[O:26])[CH:24]([NH:23][C:21]([O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:22])[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycine

Product 1

HCID 68802560HCID 68802560, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-phenylalanine ethyl ester hydrochloride (5.09 g, 22.2 mmol) and tert-butyloxycarbonylphenylglycine (5.06 g, 20.1 mmol) in N,N-dimethylformamide (100 mL) was added diisopropylethylamine (4.2 mL, 24.1 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexaflurorophosphate (9.16 g, 24.2 mmol) and the mixture stirred at ambient temperature overnight. The reaction mixture was poured into ethyl acetate (750 mL), washed with 1:1 1M aqueous hydrochloric acid/brine (2×75 mL), 1:1 saturated aqueous sodium bicarbonate solution/brine (2×75 mL), brine (200 mL), dried over sodium sulfate and concentrated in vacuo to give 2-(S)-(2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-phenyl-propionic acid ethyl ester as a pale yellow solid which still contained some N,N-dimethylformamide.

Workup

  1. washwashed with 1:1 1M aqueous hydrochloric acid/brine (2×75 mL), 1:1 saturated aqueous sodium bicarbonate solution/brine (2×75 mL), brine (200 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-573c858287c14e509b510c71aaf81e22
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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