1,2-Dichloroethane → HCID 66857138, compound

HRID 2037454Notes

Reaction equation

HRID 2037454 reaction equation
[NH2:1][CH2:2][CH2:3][C@@:4]1([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1.[C:34]([O:38][C:39]([NH:41][CH2:42][C:43](O)=[O:44])=[O:40])([CH3:37])([CH3:36])[CH3:35].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@:4]([CH2:3][CH2:2][NH:1][C:43](=[O:44])[CH2:42][NH:41][C:39](=[O:40])[O:38][C:34]([CH3:35])([CH3:36])[CH3:37])([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 53473235HCID 53473235, compound

Product 1

HCID 66857138HCID 66857138, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-6-(2-aminoethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 0.22 mmol), 2-(tert-butoxy-carbonyl-amino)acetic acid (58 mg, 0.33 mmol), HOBt (60 mg, 0.44 mmol), EDC (87 mg, 0.44 mmol) and i-Pr2NEt (142 mg, 1.1 mmol) in CH2Cl2 (5 mL) was stirred at rt overnight. After the solvents were evaporated, the crude product was purified by preparative TLC to give 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, 74%).

Workup

  1. customAfter the solvents were evaporated
  2. customthe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-ba631dab01714235b8bf5f6f30702b45
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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