L-Proline 1,1-dimethylethyl ester → 5-Amino-2-mercaptomethylpentanoyl-L-leucine

HRID 894890Notes

Reaction equation

HRID 894890 reaction equation
C(OC(=O)[C@H](CC(C)C)[NH2:8])(C)(C)C.C(OC(=O)[C@@H]1CCCN1)(C)(C)C.C([O:30][C:31](=[O:62])[C@H:32]([CH2:58][CH:59]([CH3:61])[CH3:60])[NH:33][C:34](=[O:57])[CH:35]([CH2:52][S:53]C(=O)C)[CH2:36][CH2:37][CH2:38]NC(OCC1C=CC(OC)=CC=1)=O)(C)(C)C.C(SCC(CCCN)C(N[C@H](C(O)=O)CC(C)C)=O)(=O)C.NCCCC(CS)C(N[C@H](C(O)=O)CC(C)C)=O>>[NH2:8][CH2:60][CH:59]([CH3:61])[CH2:58][C@@H:32]([C:31]([OH:30])=[O:62])[NH:33][C:34](=[O:57])[CH:35]([CH2:52][SH:53])[CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 5

HCID 6453108L-Proline 1,1-dimethylethyl esterHCID 7022311tert-butyl (2S)-2-amino-4-methylpentanoateHCID 53738373N-[2-acetylthiomethyl-5-(p-methoxybenzyloxycarbonylamino)pentanoyl]-L-Leucine tert-butyl esterHCID 53939363N-[2-acetylthiomethyl-5-aminopentanoyl]-L-leucineHCID 54226392N-(5-amino-2-mercaptomethylpentanoyl)-L-leucine

Product 1

HCID 867379575-Amino-2-mercaptomethylpentanoyl-L-leucine

Procedure

By substituting L-leucine tert-butyl ester for the proline tert-butyl ester in the procedure of Example 13, and then submitting the product to the procedure of Examples 14 and 15, N-[2-acetylthiomethyl-5-(p-methoxybenzyloxycarbonylamino)pentanoyl]-L-Leucine tert-butyl ester, N-[2-acetylthiomethyl-5-aminopentanoyl]-L-leucine and N-(5-amino-2-mercaptomethylpentanoyl)-L-leucine are obtained.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-bdd9e1d42a4541be81b76a1a6f901883
Source dataset
uspto-grants-1981_08
Patent number
US04284779

Reaction notes

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