Ethyl Acetate → HCID 20164974, compound

HRID 256043Notes

Reaction equation

HRID 256043 reaction equation
[C:1]1([CH:11]2[CH2:17][NH:16][C:15](=[O:18])[CH:14]([N:19]3[C:23](=[O:24])[C:22]4=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]4[C:20]3=[O:29])[CH2:13][S:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[H-].[Na+].C(OCC)(=O)C>CN(C)C=O.CN(C)P(=O)(N(C)C)N(C)C.O>[C:1]1([CH:11]2[CH2:17][N:16]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:15](=[O:18])[CH:14]([N:19]3[C:20](=[O:29])[C:21]4=[CH:28][CH:27]=[CH:26][CH:25]=[C:22]4[C:23]3=[O:24])[CH2:13][S:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 20164896HCID 20164896, compound

Product 1

HCID 20164974HCID 20164974, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a suspension of 3.4 g of 2-(1-naphthyl)-5-oxo-6-phthalimidoperhydro-1,4-thiazepine [prepared as described in step (e) above] in a mixture of 34 ml of dimethylformamide and 10 ml of hexamethylphosphoric triamide were added dropwise 2.25 ml of t-butyl bromoacetate and then, bit by bit, 609 mg of a 55% w/w suspension of sodium hydride in oil at 0°-5° C., under a nitrogen stream. After this addition, the reaction mixture was stirred for 16 hours at room temperature. Ethyl acetate and water were then added to the reaction mixture. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate, and the solvnet was distilled off. The residue was subjected to silica gel column chromatography using a 2:1 by volume mixture of cyclohexane and ethyl acetate as eluent, to give 2.6 g of the title compound as crystals, melting at 211°-213° C.

Workup

  1. additionAfter this addition
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvnet was distilled off
  6. additionby volume mixture of cyclohexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-1c76f7cdeb1d4f10bd0141c957fddec4
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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