Trimethylphosphine → HCID 86726381, compound

HRID 629771Notes

Reaction equation

HRID 629771 reaction equation
[N:1]([C@@H:4]([C@H:40]([C:48]1[CH:56]=[CH:55][C:51]2[O:52][CH2:53][O:54][C:50]=2[CH:49]=1)[C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:39])[C:13]=1[CH2:14][CH2:15][C@H:16]1[O:21][CH2:20][C@@H:19]([CH2:22][O:23][C:24](=[O:31])[NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])[N:18]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:17]1)=[O:6])=[N+]=[N-].CP(C)C>CCOC(C)=O.O>[NH2:1][C@@H:4]([C@H:40]([C:48]1[CH:56]=[CH:55][C:51]2[O:52][CH2:53][O:54][C:50]=2[CH:49]=1)[C:41]1[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:39])[C:13]=1[CH2:14][CH2:15][C@H:16]1[O:21][CH2:20][C@@H:19]([CH2:22][O:23][C:24](=[O:31])[NH:25][CH2:26][C:27]([F:28])([F:30])[F:29])[N:18]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:17]1)=[O:6]

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 86726379HCID 86726379, compound

Product 1

HCID 86726381HCID 86726381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from step 2 (80 mg, 0.102 mmol) in EtOAc (8 mL) and water (2 mL), was added trimethylphosphine (0.5 mL, 1M solution in THF, 0.5 mmol). The reaction mixture was stirred at ambient temperature for 2 h, then diluted with water (20 mL) and extracted with EtOAc (25 mL×3). The combined organic extracts were washed with brine (25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the title compound as colorless oil. This material was used in the next step without any additional purification. (M+H-Boc)+=682.

Workup

  1. extractionextracted with EtOAc (25 mL×3)
  2. washThe combined organic extracts were washed with brine (25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-500a4706671a48b1ae1ca7740ee6d8e6
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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