Hydrochloric Acid → HCID 67916745, compound

HRID 373761Notes

Reaction equation

HRID 373761 reaction equation
CC([C@H]1[N:9]2[CH2:10][CH2:11][CH2:12][C@:8]2([CH2:13][CH:14]=[CH2:15])[C:7](=[O:16])[O:6]1)(C)C.[ClH:17]>CO.O>[ClH:17].[CH:13]([C@:8]1([C:7]([OH:16])=[O:6])[CH2:12][CH2:11][CH2:10][NH:9]1)=[CH:14][CH3:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12860593HCID 12860593, compound

Product 1

HCID 67916745HCID 67916745, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(1,1-Dimethylethyl)-5,6,7,7a-tetrahydro-7a-(2-propenyl)-(3S-cis)-1H,3H-pyrrolo[1,2-c]oxazol-1-one (7.98 g) was dissolved in a mixture of methanol (170 ml) and water (40 ml). Silica gel (20 g) was added and the reaction was stirred for 24 h at ambient temperature. The silica was removed by filtration, washed with methanol (100 ml) and water (50 ml) and the filtrate and washes were combined, then evaporated to leave an oil which was taken up in 1M HCl (100 ml). The solution was washed with CH2Cl2 (4×50 ml) then evaporated to dryness. Residual water was removed by azeotropic evaporation with methanol to leave a brown solid (5 g) which was dried in vacuo over P2O5, leached with boiling chloroform and crystallised from methanol to give the title compound (3.68 g) m.p. 180°-183° , [α]D +50° (MeOH, C=1%).

Workup

  1. additionSilica gel (20 g) was added
  2. customThe silica was removed by filtration
  3. washwashed with methanol (100 ml) and water (50 ml)
  4. customevaporated
  5. customto leave an oil which
  6. washThe solution was washed with CH2Cl2 (4×50 ml)
  7. customthen evaporated to dryness
  8. customResidual water was removed by azeotropic evaporation with methanol

Sources & evidence

ORD record
ord-bce68223798840aca2d5cc5e5e3be273
Source dataset
uspto-grants-1992_11
Patent number
US05166136

Reaction notes

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