Water → HCID 71468675, compound

HRID 1466543Notes

Reaction equation

HRID 1466543 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:6][C@@H:7]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[C:52]([Cl:57])[C:51]=1[S:58](Cl)(=[O:60])=[O:59].O>ClCCl>[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[C:52]([Cl:57])[C:51]=1[S:58]([O:1][CH2:2][CH2:3][CH2:4][C@H:5]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:6][C@@H:7]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[NH:8][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:60])=[O:59]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5213352,4,6-Trichlorobenzenesulfonyl chlorideHCID 71468935HCID 71468935, compound

Product 1

HCID 71468675HCID 71468675, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of di-tert-butyl (4S)-4-(3-hydroxypropyl)-N-trityl-L-glutamate (438 mg, 0.78 mmol) and triethylamine (327 μL, 2.35 mmol) in dichloromethane (7.0 mL) was added 2,4,6-trichlorobenzenesulfonyl chloride (328.6 mg, 1.17 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then water was added. The organic layer was separated, and aqueous layer was extracted with dichloromethane. Combined organic solution was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (ethyl acetate/n-hexane=10/90) to give the desired product (415 mg, 66%) as a white solid.

Workup

  1. customThe organic layer was separated
  2. extractionaqueous layer was extracted with dichloromethane
  3. dry with materialCombined organic solution was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (ethyl acetate/n-hexane=10/90)

Sources & evidence

ORD record
ord-56cf7bbd43a4424d88f2420d70264232
Source dataset
uspto-grants-2015_04
Patent number
US09000037B2

Reaction notes

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