Diisopropylethylamine → HCID 86761059, compound

HRID 2242661Notes

Reaction equation

HRID 2242661 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]1)=[O:19])[C@H:9]([CH:11]1[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[F:36][C:37]([F:50])([F:49])[O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>ClCCl.C(OCC)(=O)C>[F:25][C@H:22]1[CH2:23][CH2:24][N:20]([C:18]([C@@H:8]([NH:7][C:6](=[O:26])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C@H:9]([CH:11]2[CH2:16][CH2:15][CH:14]([NH:17][S:45]([C:42]3[CH:41]=[CH:40][C:39]([O:38][C:37]([F:36])([F:49])[F:50])=[CH:44][CH:43]=3)(=[O:47])=[O:46])[CH2:13][CH2:12]2)[CH3:10])=[O:19])[CH2:21]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 131727924HCID 131727924, compound

Product 1

HCID 86761059HCID 86761059, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the material from Step B of Example 24 (32 mg, 0.085 mmol) in dichloromethane (2 mL) was added N,N-diisopropylethylamine (0.022 mL, 0.13 mmol), and 4-(trifluoromethoxy)-benzenesulfonyl chloride (0.034 mL, 0.094 mmol). After 2 h at ambient temperature the reaction was diluted with 100 mL of ethyl acetate and washed with saturated aqueous sodium bicarbonate and brine, dried (magnesium sulfate) and concentrated in vacuo. Purification by preparative thin layer chromatography (65% ethyl acetate in hexanes) afforded the title compound as a white solid. LC/MS 496.1 (M+1-Boc).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative thin layer chromatography (65% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a0c20c34ed1449128d55345f91c449c0
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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