Water → HCID 71468533, compound

HRID 1466540Notes

Reaction equation

HRID 1466540 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.[CH:49]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51][C:50]=1[S:59](Cl)(=[O:61])=[O:60].O>ClCCl>[CH:49]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51][C:50]=1[S:59]([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:61]

Participants

6

Reactant 4

HCID 962WaterHCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 71468935HCID 71468935, compound

Product 1

HCID 71468533HCID 71468533, compoundYield 98.8%

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 (217.5 mg, 0.39 mmol) and triethylamine (160 μL, 1.17 mmol) in dichloromethane (5.0 mL) was added naphthalene-2-sulfonyl chloride (155.4 mg, 0.58 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 3 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=12/88) to give the desired product (289 mg, 82%) as a white solid (m.p.=119.3° C.).

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=12/88)

Sources & evidence

ORD record
ord-f9f1e22f4d274482914cc9237f479011
Source dataset
uspto-grants-2015_04
Patent number
US09000037B2

Reaction notes

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