tert-Butanol → HCID 178453589, compound

HRID 1713883Notes

Reaction equation

HRID 1713883 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([CH2:24]C(O)=O)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:30]([CH2:33]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:42])C=CC=CC=1.[C:52]([OH:56])([CH3:55])([CH3:54])[CH3:53]>>[C:52]([O:56][C:33]([NH:30][CH2:24][C@H:21]1[CH2:22][CH2:23][C@H:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:14]=2)[CH2:19][CH2:20]1)=[O:42])([CH3:55])([CH3:54])[CH3:53]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178525562HCID 178525562, compound

Product 1

HCID 178453589HCID 178453589, compoundYield 86%

Conditions

Temperature
80 °C

Procedure

To a suspension of [trans-4-(4-{[(benzyloxy)carbonyl]amino}phenyl)cyclohexyl]acetic acid (516 mg, 1.40 mmol) in tert-butanol (3 mL) under an inert atmosphere was added triethylamine (0.45 mL, 3.23 mmol) and diphenyl phosphorylazide (0.70 mL, 3.23 mmol) and the mixture heated to 80° C. for 24 hours. Upon cooling the mixture was partitioned between EtOAc (100 mL) and H2O (20 mL). The aqueous phase was further extracted with DCM (2×20 mL) and the combined organics dried (MgSO4), filtered and evaporated. Purification by chromatography through silica gave the title compound (525 mg, 86%) as a white solid. 1H NMR (CDCl3) δ 0.96-1.07 (2H, m), 1.30-1.44 (12H, m), 1.78-1.85 (4H, m), 2.33-2.39 (1H, m), 2.94 (2H, t), 4.52 (1H, s), 5.12 (2H, s), 6.51 (1H, s), 7.04-7.07 (2H, m), 7.19-7.34 (7H, m)

Workup

  1. temperatureUpon cooling the mixture
  2. customwas partitioned between EtOAc (100 mL) and H2O (20 mL)
  3. extractionThe aqueous phase was further extracted with DCM (2×20 mL)
  4. dry with materialthe combined organics dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography through silica

Sources & evidence

ORD record
ord-2785eb683887493585ec1f7d67ed0e32
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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