Methanol → HCID 67504736, compound

HRID 1623043Notes

Reaction equation

HRID 1623043 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 (9), 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 the whole was extracted with sodium carbonate solution. Purification by means of flash chromatography (n-heptane/ethyl acetate 7:3) yielded 2.76 g (50% yield) of methyl 2-benzyloxycarbonylamino-3-diphenylaminopropionate (10).

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. extractionthe whole was extracted with sodium carbonate solution
  5. customPurification by means of flash chromatography (n-heptane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-974ddac09d584138b54ae1f41d0d0b9e
Source dataset
uspto-grants-2014_07
Patent number
US08778955B2

Reaction notes

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