Water → HCID 71468674, compound

HRID 1466541Notes

Reaction equation

HRID 1466541 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.[N:49]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][C:57]=2[S:59](Cl)(=[O:61])=[O:60])[CH:52]=[CH:51][CH:50]=1.O>ClCCl>[N:49]1[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][C:57]=2[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]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:61])=[O:60])[CH:52]=[CH:51][CH:50]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 292208-Quinolinesulfonyl chlorideHCID 71468935HCID 71468935, compound

Product 1

HCID 71468674HCID 71468674, compoundYield 51.8%

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 (203.4 mg, 0.36 mmol) and triethylamine (150 μL, 1.09 mmol) in dichloromethane (5.0 mL) was added quinoline-8-sulfonyl chloride (124.1 mg, 0.55 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 3 h and at room temperature for overnight 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 (MeOH/CH2Cl2=1/99) to give the desired product (140 mg, 51%) 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 (MeOH/CH2Cl2=1/99)

Sources & evidence

ORD record
ord-93f3681b4ad4455fa1aebd7381556cc6
Source dataset
uspto-grants-2015_04
Patent number
US09000037B2

Reaction notes

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