Potassium Carbonate → di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)hexanedioate

HRID 591338Notes

Reaction equation

HRID 591338 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:8][CH2:9][CH:10]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([S:48]([O:51][CH2:52][C@H:53]2[C@H:57]([CH2:58]OS(C3C=CC(C)=CC=3)(=O)=O)[O:56][C:55]([CH3:71])([CH3:70])[O:54]2)(=[O:50])=[O:49])=[CH:44][CH:43]=1>CN(C=O)C.[Cl-].[Na+].O>[C:30]([O:29][C:27]([NH:26][C@@H:7]([CH2:8][CH2:9][CH:10]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:58][C@H:57]2[C@H:53]([CH2:52][O:51][S:48]([C:45]3[CH:46]=[CH:47][C:42]([CH3:41])=[CH:43][CH:44]=3)(=[O:50])=[O:49])[O:54][C:55]([CH3:70])([CH3:71])[O:56]2)=[CH:23][CH:24]=1)[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:34])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 974391,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-, 4,5-bis(4-methylbenzenesulfonate), (4S,5S)-HCID 70957101Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-hydroxybenzyl)hexanedioate

Product 1

HCID 117812714di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)hexanedioateYield 53.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

500 mg (1.04 mmol) (2S)-2-tert.-Butoxycarbonylamino-5-(4-hydroxy-benzyl)-hexanedioic acid di-tert.-butyl ester, 144 mg (1.04 mmol) potassium carbonate and 491 mg (1.04 mmol) [(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene) bis(4-methylbenzenesulfonate) in 12 mL DMF were heated in a microwave at 100° C. for 2 h. Brine (300 mL) was added and the mixture was extracted with dichloromethane (3×100 mL). The combined organic fractions were dried over sodium sulfate and concentracted. The crude product was purified by Flash chromatography (Silica, 2-40% ethyl acetate in hexane) to afford 430 mg (52%) di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-{[(4S,5S)-2,2-dimethyl-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,3-dioxolan-4-yl]methoxy}benzyl)hexanedioate.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×100 mL)
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. customThe crude product was purified by Flash chromatography (Silica, 2-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-04993b20b76347179af6d64620c8cf04
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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