Trimethyl phosphite → Dimethyl {[({[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl)oxy]methyl}phosphonate

HRID 1013534Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:35]=[CH:34][C:26]([CH2:27][NH:28][C:29](=[O:33])[O:30][CH2:31]Cl)=[CH:25][CH:24]=1)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[P:36]([O:41]C)([O:39][CH3:40])[O:37][CH3:38]>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:35]=[CH:34][C:26]([CH2:27][NH:28][C:29]([O:30][CH2:31][P:36](=[O:41])([O:39][CH3:40])[O:37][CH3:38])=[O:33])=[CH:25][CH:24]=1)=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Chloromethyl [4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]carbamate (0.96 g, 1.860 mmol) and trimethyl phosphite (1 ml, 8.48 mmol) were combined in a microwave vial. The vial was capped and the reaction was allowed to heat for 3.5 hours at 100° C. The reaction was cooled and diluted with dichloromethane. The residue was purified by column chromatography on silica gel eluting with EtOAc/hexane. MS: calc'd 490 (MH+-Boc), exp 490 (MH+-Boc).

Workup

customThe vial was capped
temperatureThe reaction was cooled
customThe residue was purified by column chromatography on silica gel eluting with EtOAc/hexane

Sources & evidence

ORD record: ord-07937bf38cb34f0db14ef02f6998cb5e
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Reaction notes

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