Diisopropylamine → HCID 69985687, compound

HRID 1634736Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([O:26][C:27](=[O:29])[CH3:28])[CH:5]=[CH:6][C:7]=1[O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([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(NC(C)C)(C)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[C:27]([O:26][C:4]1[CH:5]=[CH:6][C:7]([O:8][Si:9]([C:22]([CH3:25])([CH3:23])[CH3:24])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:2]([NH:1][S:38]([CH3:37])(=[O:40])=[O:39])[CH:3]=1)(=[O:29])[CH3:28]

Participants

Conditions

Temperature: -78 °C

Procedure

Acetic acid 3-amino-4-(t-butyl-diphenyl-silanyloxy)-phenyl ester (3.5 g, 8.6 mmol) was dissolved in anhydrous dichloromethane (150 mL) and anhydrous N,N-diisoproplyamine (1.5 mL) added. The solution was cooled to −78° C. and methanesulfonyl chloride (1.08 g, 9.05 mmol) added. The solution was stirred for 30 minutes and allowed to come to room temperature. The solution was stirred overnight. The reaction mixture was washed with water. The organic solvent was dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo to yield the title compound as a solid (2.8 g, 5.7 mmol).

Workup

customto come to room temperature
stirringThe solution was stirred overnight
washThe reaction mixture was washed with water
dry with materialThe organic solvent was dried over anhydrous magnesium sulfate
filtrationThe solution was filtered
customthe solvent evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-957e6e82be1c4865bdaeb039a12ad63e
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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