Methanol → HCID 67504736, compound

HRID 2374470Notes

Reaction equation

HRID 2374470 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]([NH:15][C@@H:16]([CH2:20][N:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17]([OH:19])=[O:18])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:34]O>>[CH2:5]([O:12][C:13]([NH:15][C@@H:16]([CH2:20][N:21]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:17]([O:19][CH3:34])=[O:18])=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 66749213HCID 66749213, compound

Product 1

HCID 67504736HCID 67504736, compoundYield 50%

Procedure

6.5 ml (89.1 mmol) of thionyl chloride were added dropwise, at −5° C., to 75 ml of methanol and the mixture was stirred for 15 min. 3.6 g (9.22 mmol) of 2-benzyloxycarbonylamino-3-diphenylaminopropionic acid (3), dissolved in 75 ml of methanol, were then added and the mixture was stirred at room temperature for a further 3 hours (h). After the solvents had been evaporated, the residue was taken up in ethyl acetate and extracted with sodium carbonate solution. The purification by means of flash chromatography (n-heptane/ethyl acetate 7:3) yielded 2.76 g (50% yield) of methyl 2-benzyloxycarbonylamino-3-diphenylaminopropionate (4).

Workup

  1. additionwere then added
  2. stirringthe mixture was stirred at room temperature for a further 3 hours (h)
  3. customAfter the solvents had been evaporated
  4. extractionextracted with sodium carbonate solution
  5. customThe purification by means of flash chromatography (n-heptane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-5f343e66674a4e2d9fae68df54a0843e
Source dataset
uspto-grants-2008_12
Patent number
US07462638B2

Reaction notes

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