Water → HCID 12796630, compound

HRID 372109Notes

Reaction equation

HRID 372109 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1NCC(O)=O.[O-2:11].[Mg+2].O.[CH3:14][O:15][C:16]1[CH:28]=[CH:27][C:19]([CH2:20][O:21][C:22]([N:24]=[N+]=[N-])=[O:23])=[CH:18][CH:17]=1.[O:29]1[CH2:34][CH2:33]OCC1>>[CH3:14][O:15][C:16]1[CH:28]=[CH:27][C:19]([CH2:20][O:21][C:22]([NH:24][CH:33]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:34]([OH:29])=[O:11])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 962WaterHCID 312751,4-DioxaneHCID 1175214-Methoxybenzyl azidoformateHCID 6850729Magnesium monoxideHCID 21071957HCID 21071957, compound

Product 1

HCID 12796630HCID 12796630, compound

Procedure

1.9 g. (12.5 mmol.) of DL-2-thienylglycine and 1 g. of magnesium oxide are suspended in 50 mmol. of water. After stirring for 1/2 hour, 3 g. (15 mmol.) of (p-methoxybenzyloxycarbonyl)azide in 25 ml. of dioxane are added. After stirring for 48 hours at room temperature, the mixture is filtered. The filtrate is extracted with 200 ml. of ether. The aqueous phase is layered over with an equal volume of ethyl acetate and vigorously stirred with 20 g. of ion exchange resin (Dowex 50, acid form) for 2 hours. The ethyl acetate is separated, washed with 100 ml. of water, dried and concentrated. A light oil remains as residue which crystallizes on trituration with petroleum ether. The DL-α-[[[(4-methoxyphenyl)methoxy]carbonyl]amino]-2-thiopheneacetic acid obtained melts at 153°-156°.

Workup

  1. stirringAfter stirring for 48 hours at room temperature
  2. filtrationthe mixture is filtered
  3. extractionThe filtrate is extracted with 200 ml
  4. stirringvigorously stirred with 20 g
  5. waitof ion exchange resin (Dowex 50, acid form) for 2 hours
  6. customThe ethyl acetate is separated
  7. washwashed with 100 ml
  8. dry with materialof water, dried
  9. concentrationconcentrated
  10. customcrystallizes on trituration with petroleum ether

Sources & evidence

ORD record
ord-52ab09db5f9d4485a7643ceea6663a81
Source dataset
uspto-grants-1978_05
Patent number
US04088816

Reaction notes

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