HCID 66857138, compound → HCID 58109164, compound

HRID 2037455Notes

Reaction equation

HRID 2037455 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][NH:32][C:33](=[O:43])[CH2:34][NH:35]C(=O)OC(C)(C)C)([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:44])[CH3:16])=[CH:11][CH:10]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:35][CH2:34][C:33]([NH:32][CH2:31][CH2:30][C@@:20]1([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[O:19][C:18](=[O:44])[N:17]([C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:14][CH:13]=2)[CH3:16])[CH2:22][CH2:21]1)=[O:43]

Participants

3

Reactant 1

HCID 66857138HCID 66857138, compound

Product 1

HCID 58109164HCID 58109164, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 2-(2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethylamino)-2-oxoethylcarbamate (98 mg, 0.16 mmol) in TFA/CH2Cl2 (20%, 5 mL) was stirred at 0° C. for 2 h. The solvent was evaporated to give the crude product, which was purified by preparative HPLC to afford 2-amino-N-(2-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl)acetamide (50 mg, 60%). 1H NMR (CDCl3): 1.41-1.49 (d, 3H), 2.15-2.29 (m, 5H), 2.80-2.94 (m, 2H), 3.25-3.36 (m, 1H), 3.70-3.85 (m, 2H), 5.50 (m, 1H), 6.75-6.97 (m, 7H), 7.00-7.14 (m, 3H), 7.26-7.29 (m, 1H).

Workup

  1. customThe solvent was evaporated
  2. customto give the crude product, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-d18da0e9f9044ea4930e9f58977358a7
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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