tert-Butanol → HCID 86747563, compound

HRID 1974987Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:25]([CH2:28]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:13]=1[NH:25][C:28]([O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:37])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

2-t-Butoxycarbonylamino-4-phenylthiophene-3-carboxylic acid (2.6 g, 8 mmol) was dissolved in 5 ml of tetrahydrofuran and 1.05 ml (10.4 mmol) of triethylamine, and diphenylphosphoryl azide (2.42 g, 8.8 mmol) was added. A heavy precipitate was formed, and after 1 hour at 25° C., 80 ml of dry tert-butanol was added and the mixture heated at 90° C. for eight days. The dark reaction mixture was evaporated, dissolved in methylene chloride, washed twice with IN sodium hydroxide, twice with 1N hydrochloric acid, and twice with water. Treatment of the organic phase with charcoal and evaporation yielded 1.9 g of dark oil which was not further purified, but used for the next step. 1H-NMR (CDCl3, δ) : 1. 5 (s, 3H) , 6. 8 (s, 1H), 7.4 (m, 5H).

Workup

customA heavy precipitate was formed
customThe dark reaction mixture
customwas evaporated
dissolutiondissolved in methylene chloride
washwashed twice with IN sodium hydroxide, twice with 1N hydrochloric acid
customTreatment of the organic phase with charcoal and evaporation

Sources & evidence

ORD record: ord-133afd626859417d80af3494a844ad5d
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284847

Reaction notes

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