Hydrochloric Acid → HCID 86743251, compound

HRID 231968Notes

Reaction equation

HRID 231968 reaction equation
C[Si](C)(C(C)(C)C)[O:3][C@@H:4]([C@@H:6]1[C@@H:9]([S:10][CH2:11][CH3:12])[N:8]([C:13](=[C:27]([O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:43][Si](C3C=CC=CC=3)(C3C=CC=CC=3)C(C)(C)C)=[O:42])=[CH:37][CH:36]=2)[C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[S:15])[C:7]1=[O:61])[CH3:5].Cl>O1CCCC1>[C:41]([C:38]1[CH:37]=[CH:36][C:35]([O:34][C:27]([C:28](=[O:33])[C:29]([CH3:31])([CH3:30])[CH3:32])=[C:13]([N:8]2[C@H:9]([S:10][CH2:11][CH3:12])[C@@H:6]([C@H:4]([OH:3])[CH3:5])[C:7]2=[O:61])[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[S:15])=[CH:40][CH:39]=1)([OH:43])=[O:42]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86743252HCID 86743252, compound

Product 1

HCID 86743251HCID 86743251, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 50 g of 4-nitrobenzyl 2-(3(S)-[1(R)-[dimethyl-(2-methylprop-2-yl)silyl]oxyethyl]-4(R)-ethylthioazetidin-2-on-1-yl)-3-(4-{diphenyl[2-methylprop-2-yl]silyloxycarbonyl}phenoxy)-3-trimethylacetylthiopropenoate, 500 ml of tetrahydrofuran and 100 ml of 5.5M hydrochloric acid was stirred at room temperature for 24 hours, and then partitioned between diethyl ether and water. The organic layer was washed with water, and with brine, was dried over anhydrous magnesium sulphate, and evaporated in vacuo. Chromatography of the residue over silica gel, and elution with hexane-ethyl acetate-formic acid mixtures afforded 10.2 g of the title compound.

Workup

  1. custompartitioned between diethyl ether and water
  2. washThe organic layer was washed with water
  3. dry with materialwith brine, was dried over anhydrous magnesium sulphate
  4. customevaporated in vacuo
  5. washChromatography of the residue over silica gel, and elution with hexane-ethyl acetate-formic acid mixtures

Sources & evidence

ORD record
ord-99112686a3ab47b9b3b7e2c6039ac16b
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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