Phenyl isocyanate → HCID 69943240, compound

HRID 1978061Notes

Reaction equation

HRID 1978061 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:11]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:12]([NH:14][N:15]([S:22]([CH3:25])(=[O:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(N(CC)C(C)C)(C)C.[C:39]1([N:45]=[C:46]=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C)C=O>[C:7]([O:6][C:4]([C@H:3]([C@@H:11]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:12]([NH:14][N:15]([S:22]([CH3:25])(=[O:24])=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:2][NH:1][C:46]([NH:45][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:47])=[O:5])([CH3:9])([CH3:10])[CH3:8]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 69942786HCID 69942786, compound

Product 1

HCID 69943240HCID 69943240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.8 g of 2(R)-[2-amino-1(R)-(tert-butoxycarbonyl)ethyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide prepared as described in Example 33, part (i), 0.325 ml of N,N-diisopropylethylamine and 0.21 ml of phenyl isocyanate in 10 ml of dimethylformamide was stirred at 60° C. under nitrogen for 2.5 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate and 1M hydrochloric acid. The ethyl acetate solution was separated and washed with sodium hydrogen carbonate solution and with saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with diethyl ether and there was obtained 0.705 g of 2(R)-[1(R)-(tert-butoxycarbonyl)-2-(3-phenylureido)ethyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in the form of a white solid.

Workup

  1. customprepared
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and 1M hydrochloric acid
  4. customThe ethyl acetate solution was separated
  5. washwashed with sodium hydrogen carbonate solution and with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3a057a69bf284350bf1b4460556e9a2f
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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