Tributylphosphine → HCID 86605953, compound

HRID 1434517Notes

Reaction equation

HRID 1434517 reaction equation
O[CH2:2][C@H:3]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:4][C:5](=[O:21])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C:14]2=[O:19])=[CH:9][C:8]=1[F:20].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[F:20][C:8]1[CH:9]=[C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C:14]2=[O:19])[CH:11]=[CH:12][C:7]=1[N:6]1[C:5](=[O:21])[CH2:4][C@@H:3]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 86605954HCID 86605954, compound

Product 1

HCID 86605953HCID 86605953, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

310 mg (0.7 mmol) benzyl (2-hydroxy-(1R)-1-{[2-fluoro-4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-methyl}-ethyl)-carbamate are dissolved in 3.5 ml THF. While cooling with ice a mixture of 205 mg (0.89 mmol) di-tert.-butyl azodicarboxylate and 210 μl (0.83 mmol) tributylphosphine in 6 ml THF is added. The mixture is slowly heated to ambient temperature and stirred for 16 hours. The mixture is then evaporated to dryness. The residue is purified by reversed-phase chromatography.

Workup

  1. temperatureWhile cooling with ice
  2. additionis added
  3. customThe mixture is then evaporated to dryness
  4. customThe residue is purified by reversed-phase chromatography

Sources & evidence

ORD record
ord-4e7d7d801f94486b899341330257843e
Source dataset
uspto-grants-2009_11
Patent number
US07615549B2

Reaction notes

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