Dimethylformamide dimethyl acetal → HCID 57064189, compound

HRID 37277Notes

Reaction equation

HRID 37277 reaction equation
[C:1]([C@@H:4]1[CH2:8][C@@H:7]([S:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][N:5]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:30])(=[O:3])[NH2:2].CO[CH:44](OC)[N:45](C)C>>[N+:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][O:31][C:29]([N:5]2[CH2:6][C@@H:7]([S:9][C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][C@H:4]2[C:1]2[O:3][N:45]=[CH:44][N:2]=2)=[O:30])=[CH:34][CH:35]=1)([O-:41])=[O:40]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57099129HCID 57099129, compound

Product 1

HCID 57064189HCID 57064189, compound

Conditions

Temperature
70 °C

Procedure

To (2S, 4R)-2-Carbamoyl-1-(4-nitrobenzyloxycarbonyl)-4-(tritylthio) pyrrolidine (2 g) was added N,N-dimethylformamide dimethyl acetal (1 ml) and the mixture was stirred at 70° C. for 1 hour, and evaporated in vacuo. The oily residue was dissolved in acetic acid (20 ml) and to this solution were added sodium acetate (0.43 g) and hydroxylamine hydrochloride (0.37 g) at room temperature. After stirring at 70° C. for 1 hour, the mixture was poured into water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine successively, and dried over magnesium sulfate. After the solvent was evaporated, the residue was subjected to a column chromatography on silica gel and eluted with a mixture of acetone and dichloromethane (1:20, V/V) to give (2S ,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(1,2,4-oxadiazol-5-yl)-4-(tritylthio)pyrrolidine (1.16 g).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe oily residue was dissolved in acetic acid (20 ml) and to this solution
  3. additionwere added sodium acetate (0.43 g) and hydroxylamine hydrochloride (0.37 g) at room temperature
  4. stirringAfter stirring at 70° C. for 1 hour
  5. additionthe mixture was poured into water and ethyl acetate
  6. washThe organic layer was washed with saturated sodium bicarbonate and brine successively
  7. dry with materialdried over magnesium sulfate
  8. customAfter the solvent was evaporated
  9. washeluted with a mixture of acetone and dichloromethane (1:20, V/V)

Sources & evidence

ORD record
ord-7b543592a96f4632b3b351c875ae82d8
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

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