Acetyl chloride → HCID 59596677, compound

HRID 2264823Notes

Reaction equation

HRID 2264823 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][C@H:11]([NH:16]C(OC(C)(C)C)=O)[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C(Cl)(C)=O>CCOC(C)=O.CO>[NH2:16][C@@H:11]([CH2:10][C:9]#[C:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 59596703HCID 59596703, compound

Product 1

HCID 59596677HCID 59596677, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (2S)-5-(4-bromophenyl)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D74, 1.199 g, 3.136 mmol) in dry EtOAc (18 ml) and dry methanol (2 ml) was added AcCl (1.14 ml, 1.25 g, 15.98 mmol). After solvent removal the residue was purified using a SCX cartridge affording the title compound (849 mg, 95%). UPLC: Rt 0.51 min, MS: (ES/+) m/z: 282, 284 [MH+], C12H12BrNO2 requires 282.

Workup

  1. customAfter solvent removal the residue
  2. customwas purified

Sources & evidence

ORD record
ord-4926c98b4d204c85b9df5c775cf8541d
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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