L-Proline → HCID 54277982, compound

HRID 1607092Notes

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.[NH:36]1[CH2:43][CH2:42][CH2:41][C@H:37]1[C:38]([OH:40])=[O:39]>>[C:38]([C@@H:37]1[CH2:41][CH2:42][CH2:43][N:36]1[C:12]([S:11][CH2:10][CH2:9][NH2:8])=[O:13])([OH:40])=[O:39]

Participants

Reactant 2

HCID 145742L-Proline

HCID 15616513HCID 15616513, compound

Product 1

HCID 54277982HCID 54277982, compoundYield 159.8%

Procedure

N-triphenylmethyl-2-paranitrophenoxycabonylthioethylamine (300 mg) and L-proline (356 mg) were subjected to similar reactions to those described in References 2 and 4 to give 2-((S)-2-carboxypyrrolidino)carbonylthioethylamine (crude formate: 216 mg). The product was dissolved in anhydrous methanol (5 ml). Triethylamine (573 μl) and mitomycin A (287 mg: 1.0 molar equivalent) were added to the reaction solution which was then treated in a similar manner to that described in Example 1 to obtain Compound 31 (112 mg) in the form of grayish blue powders with a yield of 51%.

Sources & evidence

ORD record: ord-1b38dd35cd074d7ab623390c38e24700
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863935

Reaction notes

Loading…