Benzyl chloroformate → HCID 53766944, compound

HRID 2352310Notes

Reaction equation

HRID 2352310 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([S:24]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=3)(=[O:26])=[O:25])[CH:22]=2)[NH:17][CH:16]=1>C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:35]([O:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][S:24]([C:21]2[CH:22]=[C:23]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[C:15]3[CH2:14][CH2:13][NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)(=[O:26])=[O:25])=[CH:29][CH:30]=1)[CH3:36]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 19844114HCID 19844114, compound

Product 1

HCID 53766944HCID 53766944, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

Benzyl chloroformate (1.55 ml) was added portionwise to a stirred solution of the product of Example 4 (4.3 g) in a mixture of ethyl acetate (100 ml) and sodium carbonate (2 N, 100 ml) and the resulting mixture stirred at room temperature for 1 h. The aqueous layer was extracted with ethyl acetate (100 ml), the organic extracts combined, washed with hydrochloric acid (1 N, 100 ml), sodium carbonate (2 N, 100 ml) dried (MgSO4) and evaporated in vacuo to give an oil. The oil was purified by flash chromatography eluted with chloroform:methanol (19:1) to give the title compound as a foam which collapsed to a gum (2.4 g) T.l.c. Silica, Chloroform-methanol (19:1) det. u.v.+CeIVRf 0.34

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
  2. washwashed with hydrochloric acid (1 N, 100 ml), sodium carbonate (2 N, 100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto give an oil
  6. customThe oil was purified by flash chromatography
  7. washeluted with chloroform:methanol (19:1)

Sources & evidence

ORD record
ord-3edf791a082e4f9081559f73536f241a
Source dataset
uspto-grants-1989_10
Patent number
US04876267

Reaction notes

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