Dicyclohexylcarbodiimide → HCID 54470145, compound

HRID 429749Notes

Reaction equation

HRID 429749 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH2:22])=[O:21])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCC[C@H]1C(N[CH2:31][C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:33])=O.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([NH:22][CH2:31][C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:33])=[O:21])=[O:17])[CH2:10][C:11]1[N:12]=[CH:13][S:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 20706103HCID 20706103, compoundHCID 54269592HCID 54269592, compound

Product 1

HCID 54470145HCID 54470145, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-3-(4-thiazolyl)-L-alanine (1, 480 mg, 1.76 mmol) which was synthesized in accordance with the method described in the literature (Synthtic Commun., 20, 3507, (1990)), the compound (10) (650 mg, 1.76 mmol), and N-hydroxybenzotriazole (70 mg, 0.528 mmol) in N,N-dimethylformamide (20 ml) was added DCC (380 mg, 1.848 mmol) and the resulting mixture was stirred overnight at room temperature. After the precipitation which appeared was filtered off, the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and the precipitation which appeared was filtered off again. The filtrate was concentrated in vacuo. The residue was subjected to silica gel column chromatography (ethyl acetate:toluene=9:1) to give 1.02 g of the compound (13).

Workup

  1. customAfter the precipitation which
  2. filtrationappeared was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customthe precipitation which
  6. filtrationappeared was filtered off again
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c05601f53fda41d19200e00168f709af
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

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