Hydrochloric Acid → HCID 57925981, compound

HRID 1013471Notes

Reaction equation

C([O:3][P:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:35])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:19]=[CH:18][C:17]=2[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:10][CH:9]=1)([CH3:6])=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1.CCOC(C)=O>[C:31]([O:30][C:28]([NH:27][C:17]1[CH:18]=[CH:19][C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[CH:21][C:16]=1[NH:15][C:14]([C:11]1[CH:10]=[CH:9][C:8]([CH2:7][P:4]([CH3:6])(=[O:3])[OH:5])=[CH:13][CH:12]=1)=[O:35])=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution [4-(2-tert-butoxycarbonylamino-5-thiophen-2-yl-phenylcarbamoyl)-benzyl]-methyl-phosphinic acid ethyl ester (377 mg, 0.733 mmol) in dioxane (2 mL) was added NaOH (1 mL, 5.00 mmol, 5M) and the solution was heated to 60° C. After 18 h, the reaction was diluted with EtOAc, acidified with 1N HCl. The organic layer was dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The material was used without further purification. 1H NMR (DMSO-d6) δ 9.94 (s, 1H), 8.74 (br s, 1H), 7.91 (d, J=8.2 Hz, 2H), 7.79 (d, J=2.0 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.50 (dd, J=5.0, 1.2 Hz, 1H), 7.48 (dd, J=8.5, 2.0 Hz, 1H), 7.44-7.39 (m, 3H), 7.10 (dd, J=5.3, 3.5 Hz, 1H), 3.13 (d, J=17.9 Hz, 2H), 1.43 (s, 9H), 1.21 (d, J=13.8 Hz, 3H). MS: cal'd 387 (MH+; -Boc), exp 387 (MH+; -Boc).

Workup

dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe material was used without further purification

Sources & evidence

ORD record: ord-e930d260ae114202a5383d8ed4be5998
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Reaction notes

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