HCID 131722571, compound → HCID 21996067, compound

HRID 1978032Notes

Reaction equation

HRID 1978032 reaction equation
CC(C)(OC([O:7][N:8]([CH:16]([CH3:35])[CH2:17][CH2:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)(=[O:21])=[O:20])C(=O)OC(C)(C)C)=O)C>ClCCl>[OH:7][NH:8][CH:16]([CH3:35])[CH2:17][CH2:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)(=[O:20])=[O:21]

Participants

3

Reactant 1

HCID 131722571HCID 131722571, compound

Product 1

HCID 21996067HCID 21996067, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of Example 120B (1.59 g, 3.05 mmol) in 20 mL of dichloromethane at 0° C. was treated with trfluoroacetic acid (5 mL), stirred at 23° C. for 1 hour, concentrated, dissolved in ethyl acetate, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated. Purification on silica gel with 5% methanol/dichloromethane provided 820 mg (84%) of the desired product.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-df63a398ded0473e8dd64d2534828021
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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