Methanol → HCID 59596705, compound

HRID 2264820Notes

Reaction equation

HRID 2264820 reaction equation
C(Cl)(=O)C.[C:5]([C:7]1[CH:8]=[C:9]([C:22]#[C:23][CH2:24][C@H:25]([NH:30]C(OC(C)(C)C)=O)[C:26]([O:28][CH3:29])=[O:27])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])#[N:6].CO>C(OCC)(=O)C>[NH2:30][C@@H:25]([CH2:24][C:23]#[C:22][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:7]([C:5]#[N:6])[CH:8]=1)[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 59596709HCID 59596709, compound

Product 1

HCID 59596705HCID 59596705, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetyl chloride (225 ul, 248 mg, 3.16 mmol) was added dropwise to a solution of methyl (2S)-5-(3-cyano-4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D70, 286 mg, 0.631 mmol), prepared with analogous procedure to that described hereinabove, in dry ethyl acetate (10 ml) and dry methanol (2 ml). After stirring at room temperature overnight the solvent was evaporated, water (10 ml) and dioxin (10 ml) were added and the pH was adjusted to 10 using 28% NH3 in water. The mixture was extracted with DCM. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was used in the next step. MS: (ES/+) m/z: 353 [MH+], C20H17FN2O3 requires 352.

Workup

  1. customprepared with analogous procedure to that
  2. customwas evaporated
  3. additionwater (10 ml) and dioxin (10 ml) were added
  4. extractionThe mixture was extracted with DCM
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2675a0f2b4c74ce4b645a0f289022cd2
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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