Water → HCID 70563422, compound

HRID 2287175Notes

Reaction equation

HRID 2287175 reaction equation
[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[NH:6]1)([O:3][CH3:4])=[O:2].N1C=CC=CC=1.Cl[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].O>O1CCCC1.C(OCC)(=O)C>[C:1]([CH:5]1[O:11][CH:10]2[CH:7]([C:8](=[O:26])[N:9]2[C:12](=[C:23]([CH3:24])[CH3:25])[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[N:6]1[C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])([O:3][CH3:4])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 13019671HCID 13019671, compound

Product 1

HCID 70563422HCID 70563422, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 360 mg of benzyl α-(3ξ-carbomethoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 5 ml of tetrahydrofuran are added 0.1 ml of pyridine and then 255 mg of benzyl chloroformate under ice-cooling, and the mixture stirred for 90 minutes, and then mixed with water and ethyl acetate. The organic layer is separated, washed with water, dried and concentrated to yield the residue, which is chromatographed on silica gel containing 10% water to yield 306 mg of benzyl α-(3ξ-carbomethoxy-2-carbobenzoxy-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 61.7% yield.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customto yield the residue, which
  6. customis chromatographed on silica gel containing 10% water

Sources & evidence

ORD record
ord-f8b0b9d4f4364861b706f402a451a389
Source dataset
uspto-grants-1981_05
Patent number
US04269773

Reaction notes

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