반응 #57345

ord-3abb329487204045b62077784fae65ca

반응 방정식

C[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1COC1Cc2ccccc2C1)C1CCCCC1)N(C)C(=O)OC(C)(C)C
((S)-1-{(S)-1-Cyclohexyl-2-[(S)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CN[C@@H](C)C(=O)N[C@H](C(=O)N1CCC[C@H]1COC1Cc2ccccc2C1)C1CCCCC1
methylamine
수율 21.7%
CN[C@@H](C)C(=O)N[C@H](C(=O)N1CCC[C@H]1COC1Cc2ccccc2C1)C1CCCCC1
(S)-N-{(S)-1-Cyclohexyl-2-[(S)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-2-methylamino-propionamide
수율 21.7%

반응물

C[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1COC1Cc2ccccc2C1)C1CCCCC1)N(C)C(=O)OC(C)(C)C
((S)-1-{(S)-1-Cyclohexyl-2-[(S)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid

시약

없음

용매

ClCCl
DCM

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    농축The reaction mixture is concentrated in vacuo
  2. 2
    기타purified by preparative reverse-phase hplc

실험 절차

((S)-1-{(S)-1-Cyclohexyl-2-[(S)-2-(indan-2-yloxymethyl)-pyrrolidin-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (Q) (0.54 g, 1 mmol) is dissolved in DCM (8 mL) and treated with trifluoroacetic acid (4 mL) for 45 minutes. The reaction mixture is concentrated in vacuo, purified by preparative reverse-phase hplc to give 0.096 g of the methylamine (34) as a clear gum: LCMS (ES) 442.26 (MH+).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07419975B2uspto-grants-2008_09