Dicyclohexylcarbodiimide → HCID 68875593, compound

HRID 1726427Notes

Reaction equation

HRID 1726427 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24].[CH:25]1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[O:23]=[C:22]1[CH2:21][CH2:20][C:19](=[O:24])[CH:25]1[O:15][C:14](=[O:16])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:10][CH:11]([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 68875593HCID 68875593, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the mixture of N-(tert-Butoxycarbonyl)-L-leucine (1.03 g, 4.46 mmol) and N-Hydroxysuccinimide (0.74 g, 6.43 mmol) in acetonitrile (30 ml) was added 1,3-Dicyclohexylcarbodiimide (1.24 g, 6.01 mmol) and stirred for 4 hr, at room temperature. The resulting precipitate was filtered off and the acetonitrile filtrate containing 2 was carried on to the next step. MS, m/z (relative intensity): 327 [M+1H, 100%], 327 [M+1H —C(CH3)3, 100%].

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. additionthe acetonitrile filtrate containing 2

Sources & evidence

ORD record
ord-49d9108e11f44d438948b8fd02af4513
Source dataset
uspto-grants-2009_02
Patent number
US07491835B2

Reaction notes

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