Tert-butoxycarbonylalanine → N-[N-(Dec-4enoyl)-L-alaninyl]-L-phenylalanine Methyl Ester

HRID 983258Notes

Reaction equation

HRID 983258 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH2:8].C(N[C@H:27]([C:29]([OH:31])=O)[CH3:28])(OC(C)(C)C)=O.CO[C:34](=O)[C@H:35]([CH2:37][C:38]1C=C[CH:41]=[CH:40][CH:39]=1)N>CO.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:5][C:6](=[O:10])[C@H:7]([CH3:9])[NH:8][C:29](=[O:31])[CH2:27][CH2:28][CH:34]=[CH:35][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 736234L-Phenylalanine, methyl esterHCID 12988705Alanylphenylalanine methyl ester

Product 1

HCID 54300131N-[N-(Dec-4enoyl)-L-alaninyl]-L-phenylalanine Methyl Ester

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Following General Procedure A and using N-(L-alaninyl)-L-phenylalanine methyl ester (prepared by coupling N-BOC-L-alanine (Sigma) and L-phenylalanine methyl ester (Sigma) using General Procedure A, followed by removal of the BOC-group using General Procedure Y) and dec-4-enoic acid (prepare from ethyl dec-4-enoate (ICM) using General Procedure N), the title compound was prepared as a solid (mp=115.5-117.5° C.). The reaction was monitored by tlc (Rf=0.52 in 50% EtOAc/hexanes; 0.60 in 10% CH3OH/CH2Cl2) and the product was purified by flash chromatography using 10% CH3OH/CH2Cl2 as the eluent.

Workup

  1. customprepared
  2. customfollowed by removal of the BOC-group
  3. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-0ee961f042b14e14ada76f30ade5c88f
Source dataset
uspto-grants-2005_03
Patent number
US06861558B2

Reaction notes

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