Isobutyl chloroformate → HCID 86596238, compound

HRID 491013Notes

Reaction equation

HRID 491013 reaction equation
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])=[O:5].Cl[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18]>CC(N(C)C)=O>[CH2:20]([O:19][C:17]([S:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])=[O:5])=[O:18])[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 69062153HCID 69062153, compound

Product 1

HCID 86596238HCID 86596238, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-(2-mercaptobenzoyl)-L-alaninamide (0.22 g, 1.00 mmol) in DMA (5 ml) was added iso-butyl chloroformate (0.2 g, 1.50 mmol), and the mixture was stirred for 8 h. The solvent was evaporated to dryness, and the residue was triturated with ethyl ether (25 ml). The precipitate obtained was filtered, washed with water and dried over CaCl2. Yield, 73%. The product was further purified by column chromatography on silica using chloroform-methanol (7:3 v/v) as eluent with 82% recovery. 1H NMR (DMSO-d6): 0.94(d, 6H, 2CH3), 1.34(d, 3H, CH3), 1.96(m, 1H, CH), 4.06(d, 2H, CH2), 4.44quintet, 1H, CH), 7.16(brs, 1H, NH2), 7.38(brs, 1H, NH2), 7.54-7.80(m, 4H, Ar—H), 8.42(d, 1H, NH).

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe residue was triturated with ethyl ether (25 ml)
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. dry with materialdried over CaCl2
  7. customYield
  8. customThe product was further purified by column chromatography on silica

Sources & evidence

ORD record
ord-08fa8fdac5d64c7ebd4301a7d556a7e2
Source dataset
uspto-grants-2009_05
Patent number
US07528274B2

Reaction notes

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