Benzyl chloroformate → HCID 86596940, compound

HRID 2225233Notes

Reaction equation

HRID 2225233 reaction equation
[CH2:1]([C@H:5]1[C@@H:14]([NH2:15])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6]1)[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(Cl)Cl>[CH2:1]([C@@H:5]1[C@@H:14]([NH:15][C:23](=[O:24])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 69286679HCID 69286679, compound

Product 1

HCID 86596940HCID 86596940, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude (7R,8S)-7-(butyl)-8-(amino)-1,4-dioxa-spiro[4.5]decane (4.2 g, 0.02 mol) in 100 mL of CH2Cl2 was treated with an aqueous solution of K2CO3 and cooled in a ice bath. The mixture is stirred vigorously while benzyl chloroformate (3.42 g, 0.02 mol) is added slowly. After the addition is complete the mixture is stirred an additional 30 min. The organic layer is separated and washed with water, brine and concentrated. The residue was chromatographed on silica gel to give 3 g of benzyl ((7S,8S)-7-(butyl)-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamate.

Workup

  1. temperaturecooled in a ice bath
  2. additionis added slowly
  3. additionAfter the addition
  4. customThe organic layer is separated
  5. washwashed with water, brine
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-36018f95d93043dd8290bf803485c465
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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