Methyl L-phenylalaninate hydrochloride → N-[N-(Cyclopropylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

HRID 2180801Notes

Reaction equation

[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.[CH3:8][O:9][C:10](=[O:25])[C@H:11]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH2:15].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N>>[CH3:8][O:9][C:10](=[O:25])[C@H:11]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:12][C:13](=[O:17])[C@H:14]([CH3:16])[NH:15][C:5](=[O:7])[CH2:4][CH:1]1[CH2:2][CH2:3]1

Participants

Reactant 4

HCID 75736Methyl L-phenylalaninate hydrochloride

HCID 85082Tert-butoxycarbonylalanine

HCID 138440Cyclopropaneacetic acid

HCID 12988705Alanylphenylalanine methyl ester

Product 1

HCID 22895032N-[N-(Cyclopropylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

Procedure

Following General Procedure U and using cyclopropylacetic acid (Lancaster) and N-(L-alaninyl)-L-phenylalanine methyl ester (prepared by coupling N-BOC-L-alanine (Bachem) with L-phenylalanine methyl ester hydrochloride (Bachem) using General Procedure U, followed by removal of the BOC-group using General Procedure Y), the title compound was prepared as a solid (mp=128-131° C.). The reaction was monitored by tlc (Rf=0.14 in 1:1 EtOAc/hexanes).

Workup

customprepared
customfollowed by removal of the BOC-group
customwas prepared as a solid (mp=128-131° C.)

Sources & evidence

ORD record: ord-14a39d515ac640d19b92512566b92294
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06888022B2

Reaction notes

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