tert-Butanol → HCID 19100795, compound

HRID 1974971Notes

Reaction equation

[C:1]([C:3]1[C:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:5](C(O)=O)[S:6][C:7]=1[S:8][CH3:9])#[N:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>>[C:1]([C:3]1[C:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[C:5]([NH:40][C:43]([O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:28])[S:6][C:7]=1[S:8][CH3:9])#[N:2]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 19100698HCID 19100698, compound

Product 1

HCID 19100795HCID 19100795, compound

Procedure

Reaction of 4-cyano-5-methylthio-3-(t-butoxycarbonylamino)thiophene-2-carboxylic acid (9.2 g, 29 mmol), diphenylphosphoryl azide (10.0 g, 36.5 mmol) and triethylamine (4 ml, 29 mmol) in t-butyl alcohol (675 ml) was performed following the procedure outlined in example 1 (Method C). The crude product was purified by flash chromatography on silica gel 60 eluting with toluene graduated to dichloromethane. Recrystallization from toluene/petroleum ether gave 3.0 g of di-t-butyl 4-cyano5-(methylthio)thiophene-2,3-dicarbamate. M.p. 156°-157° C. 1H-NMR (CDCl3, δ): 1.50 (s, 18H), 2.55 (s, 3H), 6.55 (s, 1H), 8.30 (s, 1H).

Workup

customThe crude product was purified by flash chromatography on silica gel 60 eluting with toluene
customRecrystallization from toluene/petroleum ether

Sources & evidence

ORD record: ord-d740742f164f494b82ce8f0e5d07d22a
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284847

Reaction notes

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