tert-Butanol → HCID 53762396, compound

HRID 1974998Notes

Reaction equation

HRID 1974998 reaction equation
[C:1]([O:5][C:6]([N:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:9]1[C:13]([C:14]#[N:15])=[CH:12][S:11][C:10]=1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:28]([CH2:31]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.[CH3:50][C:51]([OH:54])([CH3:53])[CH3:52]>>[C:1]([O:5][C:6]([N:8]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[C:9]1[C:13]([C:14]#[N:15])=[CH:12][S:11][C:10]=1[NH:28][C:31]([O:54][C:51]([CH3:53])([CH3:52])[CH3:50])=[O:40])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19100731HCID 19100731, compound

Product 1

HCID 53762396HCID 53762396, compoundYield 99%

Procedure

A mixture of 3-bis(t-butoxycarbonyl)amino-4-cyanothiophene-2-carboxylic acid (18.4 g, 50 mmol) in 2-methyl-2-propanol (400 ml), triethylamine (6.0 g, 59 mmol) and diphenylphosphoryl azide (15.5 g, 55 mmol) was heated at reflux for 17 h. The reaction mixture was concentrated in vacuo, and the residue taken up in dichloromethane which was washed with a 5% citric acid solution followed by water and a sodium bicarbonate solution. The organic phase was dried (Na2so 4) and concentrated in vacuo to give 21.7 g (99%) of 4-bis(t-butoxycarbonyl)amino-5-t-butoxycarbonylamino-3-thiophene carbonitrile as an oil. 1H-NMR (CDCl3, δ): 1.5 (s, 18H), 1.55 (s, 9H), 7.25 (br.s, 1H), 7.45 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washwas washed with a 5% citric acid solution
  5. customThe organic phase was dried (Na2so 4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4918546ebdf840b58439c92b526847e6
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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