tert-Butanol → HCID 19100744, compound

HRID 1974984Notes

Reaction equation

HRID 1974984 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]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.[CH3:47][C:48]([OH:51])([CH3:50])[CH3:49]>>[CH:17]1([C:12]2[C:13]([NH:25][C:28]([O:51][C:48]([CH3:50])([CH3:49])[CH3:47])=[O:37])=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[S:10][CH:11]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19100740HCID 19100740, compound

Product 1

HCID 19100744HCID 19100744, compoundYield 4%

Procedure

A mixture of 2-t-butoxycarbonylamino-4-cyclohexylthiophene-3-carboxylate (7.5 g, 23 mmol) in 2-methyl-2-propanol (400 ml), triethylamine (2.33 g, 23 mmol) and diphenylphosphoryl azide was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo and the residue submitted to flash chromatography using silica gel 60 eluting with toluene to give 400 mg (4%) of di-t-butyl 4-cyclohexylthiophene-2,3-dicarbamate as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f4399076535449a0bc6458d16357f287
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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