D-Proline methyl ester → HCID 53704324, compound

HRID 1607093Notes

Reaction equation

HRID 1607093 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[NH:8][CH2:9][CH2:10][S:11][C:12](OC2C=CC([N+]([O-])=O)=CC=2)=[O:13])C=CC=CC=1.[CH3:36][O:37][C:38](=[O:44])[C@H:39]1[CH2:43][CH2:42][CH2:41][NH:40]1>>[CH3:36][O:37][C:38]([C@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:12]([S:11][CH2:10][CH2:9][NH2:8])=[O:13])=[O:44]

Participants

3

Reactant 2

HCID 853476D-Proline methyl esterHCID 15616513HCID 15616513, compound

Product 1

HCID 53704324HCID 53704324, compoundYield 103.8%

Procedure

N-triphenylmethyl-2-paranitrophenoxycarbonylthioethylamine (675 mg) and D-proline methylester (0.18 g) were subjected to similar reactions to those described in References 2 and 4 to give 2-[(R)-2-methoxycarbonylpyrrolidino]carbonylthioethylamine (crude formate: 336 mg). The product was dissolved in anhydrous methanol (6 ml). To the solution were added triethylamine (1.01 ml) and mitomycin A (338 mg: 0.8 molar equivalent). The solution was then treated in a similar manner to that described in Example 1 to obtain Compound 32 (286 mg) in the form of grayish blue powders with a yield of 43%.

Sources & evidence

ORD record
ord-893da8e940dd466a838a23e70fa40be3
Source dataset
uspto-grants-1989_09
Patent number
US04863935

Reaction notes

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