Dicyclohexylcarbodiimide → Benzyl N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]carbamate

HRID 2209551Notes

Reaction equation

HRID 2209551 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10](O)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O[N:24]1C(=O)CC[C:25]1=O.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:24][CH3:25])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 13443905Benzyl N-[(1S)-1-(methylcarbamoyl)-2-phenylethyl]carbamateYield 107.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.00 g of Cbz-Phe-OH (Sigma Chemical Company), 0.385 g of N-hydroxysuccinimide and 0.541 g of 1,3-dicyclohexylcarbodiimide in 5 mL of dry THF was kept at 4° C. under N2 overnight. The resulting precipitate was removed by filtration, and to the filtrate was added excess 40% aqueous methylamine at room temperature. The mixture was stirred at room temperature for 30 min. The solid was removed by filtration and the filtrate was partitioned between saturated aqueous NaHCO3 and CH2Cl2. The organic layer was separated, dried over anhydrous Na2SO4, and evaporated under reduced pressure to give 1.12 g of the crude Cbz-Phe-NHMe.

Workup

  1. customThe resulting precipitate was removed by filtration
  2. additionto the filtrate was added excess 40% aqueous methylamine at room temperature
  3. customThe solid was removed by filtration
  4. customthe filtrate was partitioned between saturated aqueous NaHCO3 and CH2Cl2
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-516d42827f5249fe91514fd3e57b3412
Source dataset
uspto-grants-1995_10
Patent number
US05455262

Reaction notes

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