Leu-Pro → L-Alanyl-L-proline methyl ester

HRID 622635Notes

Reaction equation

N[C@H](C(N1CCC[C@H]1C(O)=O)=O)CC(C)C.N[C@H](C(N1CCC[C@H]1C(O)=O)=O)CC1C=CC=CC=1.[NH2:36][C@H:37]([C:42]([N:44]1[CH2:52][CH2:51][CH2:50][C@H:45]1[C:46]([O:48][CH3:49])=[O:47])=[O:43])[CH2:38]CSC.N[C@H](C(N1CCC[C@H]1C(OC)=O)=O)CCCC>>[NH2:36][C@H:37]([C:42]([N:44]1[CH2:52][CH2:51][CH2:50][C@H:45]1[C:46]([O:48][CH3:49])=[O:47])=[O:43])[CH3:38]

Participants

Reactant 4

HCID 80817Leu-Pro

HCID 7020642Phe-Pro

HCID 14302366H-Met-Pro-OMe

HCID 93368933H-norLeu-Pro-OMe

Product 1

HCID 11052640L-Alanyl-L-proline methyl ester

Procedure

Instead of Z-Ala-OH, (a) Z-Val-OH, (b) Z-Leu-OH, (c) Z-Phe-OH, (d) Z-Met-OH and (e) Z-norLeu-OH were used as starting compounds to obtain (a') H-Val-Pro-OMe, (b') H-Leu-Pro-OH, (c') H-Phe-Pro-OH, (d') H-Met-Pro-OMe and (e') H-norLeu-Pro-OMe as oils, respectively.

Sources & evidence

ORD record: ord-1738f47ce5f24ce3a5e1bfa5bf84b039
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772587

Reaction notes

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