Chlorotrimethylsilane → HCID 67837029, compound

HRID 1029630Notes

Reaction equation

HRID 1029630 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([C:17](=[O:27])[CH2:18][C@H:19]2[NH:22][C:21](=[O:23])[C@@H:20]2[C@H:24]([OH:26])[CH3:25])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][Si:29](Cl)([CH3:31])[CH3:30].[C:33](Cl)(=[O:37])[C:34](Cl)=[O:35].[N+:39]([C:42]1[CH:49]=[CH:48][C:45]([CH2:46][OH:47])=[CH:44][CH:43]=1)([O-:41])=[O:40]>ClCCl.O.C(OCC)(=O)C.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]=[C:14]([C:17](=[O:27])[CH2:18][C@H:19]2[N:22]([C:33](=[O:37])[C:34]([O:47][CH2:46][C:45]3[CH:44]=[CH:43][C:42]([N+:39]([O-:41])=[O:40])=[CH:49][CH:48]=3)=[O:35])[C:21](=[O:23])[C@@H:20]2[C@H:24]([O:26][Si:29]([CH3:31])([CH3:30])[CH3:28])[CH3:25])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 65578Oxalyl chlorideHCID 692754-Nitrobenzyl alcoholHCID 15117238HCID 15117238, compound

Product 1

HCID 67837029HCID 67837029, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S,4R)-4-[2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-yl)-2-oxoethyl]-3-[(1R)-1-hydroxyethyl]-2-oxoazetidine (3.59 g) and pyridine (3.9 ml in dichloromethane (3.5 ml) was added dropwise trimethylsilyl chloride (1.42 ml) at -70° C. under nitrogen atmosphere and the mixture was stirred for 1 hour. To this solution was added dropwise at -70° C. a reaction mixture of oxalyl chloride (1.26 ml) and 4-nitrobenzyl alcohol (2.3 g) in dichloromethane (10 ml) at 0° C., which solution was stirred for additional 1 hour. The reaction mixture was poured into a mixture of ethyl acetate (70 ml) and water (40 ml). The organic layer was separated, washed with water (50 ml) containing acetic acid (550 μl), and brine (50 ml) successively, and then dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (250 ml) eluting with a mixture of hexane and ethyl acetate (1:1, V/V) to give 4-nitrobenzyl 2-[(3S,4R)-4-{ 2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl}-3-{(1R)-1-trimethylsilyloxyethyl}-2-oxoazetidin-1-yl]-2-oxoacetate (4.73 g).

Workup

  1. additionTo this solution was added dropwise at -70° C.
  2. stirringwhich solution was stirred for additional 1 hour
  3. customThe organic layer was separated
  4. washwashed with water (50 ml)
  5. additioncontaining acetic acid (550 μl), and brine (50 ml) successively
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent
  8. customgave a residue, which
  9. customwas chromatographed on silica gel (250 ml)
  10. washeluting with a mixture of hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-138c38d17f3f47bdb3d6d7aaa6fb21d7
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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