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Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 46445
Notes
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Reaction equation

HRID 46445 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:24][N:25]1[C:34](=[O:35])[CH:33]2[CH:28]([CH:29]3[CH2:36][CH:32]2[CH:31]=[CH:30]3)[C:26]1=[O:27].[CH:37]1([N:43]=[C:44]=[N:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>O1CCCC1>[OH:24][N:25]1[C:34](=[O:35])[CH:33]2[CH:28]([CH:29]3[CH2:36][CH:32]2[CH:31]=[CH:30]3)[C:26]1=[O:27].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH:46]1([NH:45][C:44]([NH:43][CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)=[O:8])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 6992483N-[(Phenylmethoxy)carbonyl]-L-leucylglycine

Product 3

HCID 4277N,N'-DicyclohexylureaHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione
HCID 6992483
N-[(Phenylmethoxy)carbonyl]-L-leucylglycine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the N-hydroxy-5-norbornene-2,3-dicarboximide active ester of N-benzyloxycarbonyl-L-leucylglycine was prepared according to the general procedure of M. Fujino, et al [Chem. Pharm. Bull. Japan, 22, 1857 (1974)]. A solution of 1.27 g. of N-benzyloxycarbonylleucylglycine and 0.72 g. of N-hydroxy-5-norbornene-2,3-dicarboximide in 5 ml. of tetrahydrofuran was cooled in an ice bath and 0.83 g. of N,N'-dicyclohexylcarbodiimide was added to the cold solution together with 1 ml. of tetrahydrofuran. The reaction mixture was stirred at low temperature for 40 minutes and then at room temperature for 21/2 hours. The N,N'-dicyclohexylurea formed during the reaction was collected on a filter and washed with three 1-ml. portions of tetrahydrofuran.

Workup

  1. customat room temperature
  2. custom2 hours

Sources & evidence

ORD record
ord-183450c1dc30458ca6ef56b52fe5e039
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04173564

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes