L-Tyrosine → HCID 131729454, compound

HRID 1644160Notes

Reaction equation

HRID 1644160 reaction equation
[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:6]([NH:8][C@H:9]([C:18](OC)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14](O)=[CH:13][CH:12]=1)=[O:7])C(C)C.[NH:32](C(OCC1C=CC=CC=1)=O)[C@H:33]([C:37]([NH:39][C@H](C(OC)=O)CCCCNC(OC(C)(C)C)=O)=[O:38])[CH:34](C)C.N(C(OCC1C=CC=CC=1)=O)[C@H:68](C(N[C@H](C(N[C@@H](C(OC)=O)C)=O)CC1C=CC=CC=1)=O)C.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.N[C@H](C(O)=O)CCCCNC(OC(C)(C)C)=O.N[C@@H](C(O)=O)C>>[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C:6]([NH:8][C@H:9]([C:18]([NH:32][C@@H:33]([C:37]([NH2:39])=[O:38])[CH3:34])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])[CH3:68]

Participants

7

Reactant 6

HCID 6057L-TyrosineHCID 71080D-AlanineHCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acidHCID 12859615HCID 12859615, compoundHCID 131729455HCID 131729455, compoundHCID 131729456HCID 131729456, compound

Product 1

HCID 131729454HCID 131729454, compound

Procedure

With the exception of Z-Val-Tyr-OMe, Z-Val-Lys(Boc)-OMe and Z-Ala-Phe-D-Ala-OMe, all substrate peptides were quantitatively converted into products, i.e. the corresponding amide peptide and free carboxylic acid peptide, in 4 h reaction time. At longer reaction times also the methyl ester peptides ending with Tyr and Lys(Boc) were totally converted. Surprisingly, the methyl ester of the tripeptide with a C-terminal D-Ala residue was also converted. The HPLC analysis at 75 h reaction time showed conversion of 54 ala % of substrate to yield about 36 a/a % of the product Z-Ala-Phe-D-Ala-NH2.

Workup

  1. customin 4 h reaction time
  2. customThe HPLC analysis at 75 h reaction time

Sources & evidence

ORD record
ord-572603a2517b4f6d8bb9d0640131cd1b
Source dataset
uspto-grants-2012_02
Patent number
US08124372B2

Reaction notes

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