Acetonitrile → cis-N-Carbobenzyloxy-4-[[(methylamino)carbonyl]oxy]-L-proline, methyl ester

HRID 1856002

Reaction equation

HRID 1856002 reaction equation
[C:1]([N:11]1[CH2:19][C@@H:18]([OH:20])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(#N)C.[CH3:24][N:25]=[C:26]=[O:27]>C(N(CC)CC)C>[C:1]([N:11]1[CH2:19][C@@H:18]([O:20][C:26]([NH:25][CH3:24])=[O:27])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 12228Methyl IsocyanateHCID 688413(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 131711848cis-N-Carbobenzyloxy-4-[[(methylamino)carbonyl]oxy]-L-proline, methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 5.4 g. (0.019 mole) of N-carbobenzyloxy-cis-4-hydroxy-L-proline, methyl ester, in 120 ml. of acetonitrile is added 5.4 ml. of triethylamine, followed by 5.4 ml. of methyl isocyanate. After keeping overnight at room temperature and refluxing for two hours, the reaction mixture is worked up as in Example 1c to give 5.6 g (86%) of a pale yellow viscous oil.

Workup

  1. temperaturerefluxing for two hours

Sources & evidence

ORD record
ord-2fdfd0183bb64ac9a910b5f1b10c4985
Source dataset
uspto-grants-1980_08
Patent number
US04217359

Linked notes

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