tert-Butanol → HCID 131728321, compound

HRID 1713072Notes

Reaction equation

HRID 1713072 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([C:7]1[C:15]2[CH:14]=[CH:13][C:12](=[O:16])[N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[S:9][C:8]=1C(O)=O)=[O:6].C1(P([N:43]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[C:53]([O-:56])(O)=[O:54].[Na+].[CH3:58][C:59](O)([CH3:61])[CH3:60]>>[C:59]([O:56][C:53](=[O:54])[NH:43][C:8]1[S:9][C:10]2[N:11]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:12](=[O:16])[CH:13]=[CH:14][C:15]=2[C:7]=1[C:5](=[O:6])[C:4]1[CH:26]=[CH:27][CH:28]=[C:2]([CH3:1])[CH:3]=1)([CH3:61])([CH3:60])[CH3:58]

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 67532800HCID 67532800, compound

Product 1

HCID 131728321HCID 131728321, compoundYield 90%

Procedure

A mixture of Example 2 (4.7 g, 12.0 mmol), diphenylphosphoryl azide (3.63 g, 13 mmol) and triethylamine (1.31 g, 13 mmol) in 2-methyl-2-propanol (100 ml) was heated at 90° C. for 3 h. The reaction was cooled to r.t. and NaHCO3(aq) (200 ml) added. The mixture was extracted with DCM (3×100 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography (silica, 10% EtOAc in DCM) to give the title compound as a yellow solid (5.4 g, 90%). δH (CDCl3) 10.6 (1H, s), 7.62-7.46 (3H, m), 7.40-7.29 (6H, m), 6.81 (1H, d, J 9.7 Hz), 6.36 (1H, d, J 9.7 Hz), 2.37 (3H, s), 1.42 (9H, s). LCMS (ES+) RT 4.44 minutes, 461 (M+H)+.

Workup

  1. extractionThe mixture was extracted with DCM (3×100 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by chromatography (silica, 10% EtOAc in DCM)

Sources & evidence

ORD record
ord-2f15f252f5b849c8b23620310a4721c0
Source dataset
uspto-grants-2010_09
Patent number
US07795256B2

Reaction notes

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