Triphenylphosphine → HCID 57513677, compound

HRID 2368409Notes

Reaction equation

HRID 2368409 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:34]([O:38][C:39](=[O:68])[NH:40][CH:41]([C:45](=[O:67])[NH:46][C:47]1[S:48][C:49]([O:59][C:60]2[CH:65]=[CH:64][C:63]([F:66])=[CH:62][CH:61]=2)=[C:50]([C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=2)[N:51]=1)[CH2:42][CH2:43]O)([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[C:34]([O:38][C:39](=[O:68])[NH:40][CH:41]1[CH2:42][CH2:43][N:46]([C:47]2[S:48][C:49]([O:59][C:60]3[CH:61]=[CH:62][C:63]([F:66])=[CH:64][CH:65]=3)=[C:50]([C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=3)[N:51]=2)[C:45]1=[O:67])([CH3:35])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57513823HCID 57513823, compound

Product 1

HCID 57513677HCID 57513677, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

DIAD (0.22 mL, 1.1 mmol) was added to a solution of PPh3 (300 mg, 1.15 mmol) in THF (5 mL) at room temperature. The mixture was stirred at room temperature for 5 min. To this was added a solution of {1-[5-(4-Fluoro-phenoxy)-4-(4-fluoro-phenyl)-thiazol-2-ylcarbamoyl]-3-hydroxy-propyl}-carbamic acid tert-butyl ester (438 mg, 0.867 mmol) in THF (15 mL). The mixture was stirred at room temperature for 30 min and partitioned between EtOAc and aqueous K2CO3. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound. 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 2.10-2.20 (m, 1H), 2.79-2.87 (m, 1H), 3.87-3.95 (m, 1H), 4.35-4.41 (m, 1H), 4.45-4.52 (m, 1H), 5.08-5.13 (m, 1H), 6.95-7.08 (m, 6H), 7.90-7.95 (m, 2H). m/z 488.1 (MH+).

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min
  2. custompartitioned between EtOAc and aqueous K2CO3
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-d53d538406df40d79b71f2d2546cac46
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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