Diisopropylethylamine → HCID 13419969, compound

HRID 1262893Notes

Reaction equation

HRID 1262893 reaction equation
FC1C([O:8][C:9](=O)[C@H:10]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)[NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])=C(F)C(F)=C(F)C=1F.Cl.[C:43]1([CH2:49][CH2:50][CH2:51][NH:52][C:53](=[O:58])[C@@H:54]([CH2:56][OH:57])[NH2:55])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:15]([O:14][C:12]([NH:11][C@H:10]([C:9]([NH:55][C@@H:54]([C:53]([NH:52][CH2:51][CH2:50][CH2:49][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:58])[CH2:56][OH:57])=[O:8])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:28]=1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13118740HCID 13118740, compoundHCID 70512675HCID 70512675, compound

Product 1

HCID 13419969HCID 13419969, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-benzyloxycarbonyl-O-benzyl-L-tyrosine pentafluorophenyl ester (2.34 g.), N-(3-phenylpropyl)-D-serinamide hydrochloride (1.00 g.) and diisopropylethylamine (0.71 ml.) in tetrahydrofuran (25 ml.) was stirred at room temperature for one hour. The mixture was triturated with water, and the product was precipitated with hot ethyl acetate and recrystallized from ethyl acetate, affording (N-benzyloxycarbonyl-O-benzyl-L-tyrosyl)-N-(3-phenylpropyl)-D-serinamide (1.35 g., m.r. 175°-177° C.).

Workup

  1. customThe mixture was triturated with water
  2. customthe product was precipitated with hot ethyl acetate
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-11ea748386d64fb28bcb39922f15c18b
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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