Dicyclohexylcarbodiimide → HCID 178427497, compound

HRID 1502635Notes

Reaction equation

HRID 1502635 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[NH:10].[CH2:22]([O:29][C:30](=[O:45])[C@H:31]([CH2:40][CH2:41][C:42](O)=[O:43])[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1CCC(N=C=NC2CCCCC2)CC1>ClCCl.CN(C1C=CN=CC=1)C>[C:36]([O:35][C:33]([NH:32][CH:31]([CH2:40][CH2:41][C:42]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:14])=[O:13])=[NH:10])=[O:43])[C:30]([O:29][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:45])=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1537081-(Phenylmethyl) hydrogen N-((1,1-dimethylethoxy)carbonyl)-L-glutamateHCID 178427494HCID 178427494, compound

Product 1

HCID 178427497HCID 178427497, compoundYield 119.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.48 g (7.9 mmol, 1 eq.) of N—(N-(6-hydroxyhexyl)carbamimidoyl)-4-methylbenzenesulfonamide and 2.67 g (7.9 mmol, 1 eq.) of Boc-L-glutamic acid 1-benzyl ester were dissolved under nitrogen in dry dichloromethane. 198.9 mg (1.58 mmol, 0.2 eq.) of DMAP and 1.810 g (8.7 mmol, 1.1 eq.) of DCC were added at room temperature. The reaction was stirred overnight and a white precipitate appeared. The precipitate was removed by filtration and the solvent evaporated to afford 5.99 g of a mixed yellow oil/solid compound. This compound was purified by flash chromatography over silica (eluant pure AcOEt; Rf=0.71) to afford 4.83 g of a slightly yellow oil (yield=97%).

Workup

  1. customThe precipitate was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-5d57180876b846a6bb950232ab53ee56
Source dataset
uspto-grants-2015_12
Patent number
US09211340B2

Reaction notes

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