Dicyclohexylcarbodiimide → HCID 14407421, compound

HRID 1086590Notes

Reaction equation

HRID 1086590 reaction equation
[NH2:1][C:2]([C:18]([O:20][CH2:21][CH3:22])=[O:19])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3][C:4](=[CH2:12])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:23]([NH:30][C@H:31]([C:33](O)=[O:34])[CH3:32])([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>C(COC)OC>[CH3:29][C:26]([CH3:27])([O:25][C:23]([NH:30][C@H:31]([C:33]([NH:1][C:2]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:3][C:4](=[CH2:12])[CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:34])[CH3:32])=[O:24])[CH3:28]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 14407404HCID 14407404, compound

Product 1

HCID 14407421HCID 14407421, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 945 mg of the product of Step D of Example 1, 30 ml of dimethoxyethane and 621 mg of Boc-L-alanine was cooled to 0° C. and 678 mg of dicyclohexylcarbodiimide were added in small fractions over 10 minutes. The mixture was stirred at 0° C. for 16 hours. After filtering, the filtrate was evaporated to dryness under reduced pressure and chromatography was carried out on silica. Elution with a cyclohexane-ethyl acetate mixture (7-3) yielded 1.3 g of the expected product with a specific rotation of [α]D =-22°±2° (c=0.7% in CH2Cl2).

Workup

  1. filtrationAfter filtering
  2. customthe filtrate was evaporated to dryness under reduced pressure and chromatography
  3. washElution with a cyclohexane-ethyl acetate mixture (7-3)

Sources & evidence

ORD record
ord-be2c3171891e426fbad6a4cd82b5b477
Source dataset
uspto-grants-1991_07
Patent number
US05030715

Reaction notes

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