Dicyclohexylcarbodiimide → HCID 67834914, compound

HRID 1460495Notes

Reaction equation

HRID 1460495 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][S:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]([N:43]2[CH2:50][CH2:49][CH2:48][C@H:44]2[C:45](O)=[O:46])=[O:42])=[CH:36][CH:35]=1>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][S:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH:27][C:45]([C@@H:44]1[CH2:48][CH2:49][CH2:50][N:43]1[C:41](=[O:42])[CH2:40][C:37]1[CH:36]=[CH:35][C:34]([O:33][CH3:32])=[CH:39][CH:38]=1)=[O:46]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11254872HCID 11254872, compoundHCID 42256687HCID 42256687, compound

Product 1

HCID 67834914HCID 67834914, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,3-dicyclohexylcarbodiimide (DCC) (705 g) in dichloromethane (1400 ml) was added over 30 minutes to a stirred solution of 2-(2-bromophenylmethylthio)aniline (see Bull. Chem. Soc. Japan, 48, 2323 (1975)) (957 g) and (S)-1-(4-methoxyphenylacetyl)proline (see Preparation 24) (900 g) in dichloromethane (5.5 L). The mixture was stirred at 25°-35° C. for one hour and filtered. The filtrate was evaporated under reduced pressure to give the desired product as a brown gum which was used directly in Preparation 22.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cdb19f5875ad447ebedc4b24180d051e
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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