Isopropyl chloroacetate → HCID 57108906, compound

HRID 2165283Notes

Reaction equation

HRID 2165283 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][C@H:16]1[C@H:19]([CH3:20])[N:18]([OH:21])[C:17]1=[O:22])=[O:14])([CH3:11])([CH3:10])[CH3:9].Cl[CH2:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>CN(C)C=O>[C:8]([O:12][C:13]([NH:15][C@H:16]1[C@H:19]([CH3:20])[N:18]([O:21][CH2:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[C:17]1=[O:22])=[O:14])([CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 7759Isopropyl chloroacetateHCID 8471TriethylamineHCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate

Product 1

HCID 57108906HCID 57108906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.3 g of Triethylamine was dropped into a solution of 19.5 g of (3S-trans)-3-(t-butyloxycarbonylamino)-1-hydroxy -4-methyl-2-azetidinone and 14.8 g of chloroacetic acid, 1-methylethyl ester in 400 ml of dry dimethylformamide. The whole was stirred at room temperature for 3 days. Triethylamine hydrochloride was filtered off and the solvent was stripped at 35° C. in vacuo. The residual oil was taken up in ether, the extract was allowed to stand in the refrigerator for about two hours, filtered and the ether again evaporated in vacuo. The resulting oily title compound (30 g) containing about 2 g of impurities was used in the next step without further purification.

Workup

  1. filtrationTriethylamine hydrochloride was filtered off
  2. customwas stripped at 35° C. in vacuo
  3. waitto stand in the refrigerator for about two hours
  4. filtrationfiltered
  5. customthe ether again evaporated in vacuo
  6. additionThe resulting oily title compound (30 g) containing about 2 g of impurities
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-e562c2c0b01443a8a0ec9487b3ce2a8d
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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