Triethylamine → HCID 58109118, compound

HRID 2037595Notes

Reaction equation

HRID 2037595 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11]2=[O:27])[CH3:9])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[CH3:35][S:36]([O:19][CH2:18][CH2:17][CH2:16][C@@:13]1([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[O:12][C:11](=[O:27])[N:10]([C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH3:9])[CH2:15][CH2:14]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58109181HCID 58109181, compound

Product 1

HCID 58109118HCID 58109118, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (20 mg, 0.046 mmol) in CH2Cl2 (2 mL) was added Et3N (13 μL, 2 equiv) and MsCl (6 μL, 1.55 equiv) at 0° C. After 5 min, the mixture was warmed to rt and stirred for 1 h. The mixture was concentrated, acidified with 5% aq HCl to pH=˜6 and purified by preparative HPLC to afford 3-((R)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propyl methanesulfonate (6.8 mg, 29%). LC-MS (3 min) tR=1.83 min., m/z 514, 516 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5cdc8a97f9ee4ce7aa22e6642485ece9
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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