Formic Acid → (S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-aminopropanoate

HRID 928221Notes

Reaction equation

HRID 928221 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:17]C(OC(C)(C)C)=O)[C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=1[Cl:25])[CH:2]=[CH2:3].C(O)=O>>[CH3:16][O:15][C:13](=[O:14])[C@@H:12]([NH2:17])[CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[C:6]([Cl:25])[CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86691116(S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoate

Product 1

HCID 86691117(S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-aminopropanoate

Procedure

In a 10 mL round-bottomed flask, (S)-methyl 3-(4-(allyloxy)-3-chlorophenyl)-2-(tert-butoxycarbonylamino)propanoate (90 mg, 243 μmol, Eq: 1.00) was combined with formic acid (1.12 g, 933 μL, 24.3 mmol, Eq: 100) and stirred at RT for 3 h. The crude reaction mixture was concentrated in vacuo. The reaction mixture was neutralised with 5% aqueous Na2CO3 and extracted with DCM (3×). The organic layers were combined and dried over Na2SO4 and concentrated in vacuo to yield a colorless oil (68 mg; 100%). m/z=270.3 [M+H]+; 292.1 [M+Na]+.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated in vacuo
  3. extractionextracted with DCM (3×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto yield a colorless oil (68 mg; 100%)

Sources & evidence

ORD record
ord-4b0eba4dd6a44ff7ac431fbffd0de66d
Source dataset
uspto-grants-2016_03
Patent number
US09290467B2

Reaction notes

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