Hydrochloric Acid → HCID 18659459, compound

HRID 275602Notes

Reaction equation

HRID 275602 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([C:28]([O:30][CH3:31])=[O:29])[C:10]([S:13]([CH2:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([OH:20])=[O:19])(=[O:15])=[O:14])([CH3:12])[CH3:11])=[O:7])(C)(C)C.Cl.ClC(O[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=O>O1CCOCC1>[CH2:37]([O:5][C:6]([NH:8][C@H:9]([C:28]([O:30][CH3:31])=[O:29])[C:10]([S:13]([CH2:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([OH:20])=[O:19])(=[O:15])=[O:14])([CH3:11])[CH3:12])=[O:7])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 18659461HCID 18659461, compound

Product 1

HCID 18659459HCID 18659459, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.0g (2.19mmol) of (RS)-α-[[[(R)-2-(1-tert-butoxyformamido)-2-(methoxycarbonyl)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamic acid was added dropwise at room temperature to 10 ml of 1.4 M hydrogen chloride in dioxan and stirred for a further 12 hours. After evaporation of the solvent under reduced pressure there was obtained a colourless foam which, without further purification and characterization, was dissolved in 8.5 ml of 1N sodium hydrogen carbonate solution and treated with 0.44 ml (3.07 mmol) of benzyl chloroformate. The thus-obtained suspension was stirred at room temperature for 12 hours. Subsequently, it was extracted twice with 250 ml of ether each time, the combined ether extracts were dried over magnesium sulphate and evaporated under reduced pressure. For purification, the oily crude product (1.05 g) was chromatographed on 50 g of silica gel firstly with methylene chloride then with a 95:5 mixture of methylene chloride and methanol as the eluent. There were obtained 430 mg of (RS)-α-[[[(R)- 2-(1-benzyloxyformamido)-2-(methoxycarbonyl)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamic acid as a colourless foam, MS: 493 (M+H)+.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthere was obtained a colourless foam which
  3. customwithout further purification and characterization
  4. dissolutionwas dissolved in 8.5 ml of 1N sodium hydrogen carbonate solution
  5. stirringThe thus-obtained suspension was stirred at room temperature for 12 hours
  6. extractionSubsequently, it was extracted twice with 250 ml of ether each time
  7. dry with materialthe combined ether extracts were dried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customFor purification
  10. customthe oily crude product (1.05 g) was chromatographed on 50 g of silica gel firstly with methylene chloride
  11. additionwith a 95:5 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-dbebc3c22a274c8eaf4024f108fec41e
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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