Dimethylformamide → HCID 86750574, compound

HRID 976238Notes

Reaction equation

HRID 976238 reaction equation
ClC1C=CC(N[C:9]([NH:13][C@@H:14]2[C:19]3[CH:20]=[C:21]([P:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:27])[O:25][CH3:26])[CH:22]=[CH:23][C:18]=3[O:17][C:16]([CH3:35])([CH3:34])[C@H:15]2[OH:36])=[N:10][C:11]#[N:12])=CC=1.N[C@@H:38]1[C:43]2C=C(P(C3C=CC=CC=3)(=O)OC)C=CC=2O[C:40](C)(C)[C@H:39]1O.CN(C=[O:65])C>C(OCC)(=O)C>[OH:36][C@H:15]1[C@H:14]([NH:13][C:9]([NH:10][C:11]2[CH:40]=[CH:39][CH:38]=[CH:43][N:12]=2)=[O:65])[C:19]2[CH:20]=[C:21]([P:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])[O:25][CH3:26])[CH:22]=[CH:23][C:18]=2[O:17][C:16]1([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10736408HCID 10736408, compoundHCID 178502939HCID 178502939, compound

Product 1

HCID 86750574HCID 86750574, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the title G compound of Example 1 ((3S-trans)-(4-Amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)phenylphosphinic acid, methyl ester (300 mg, 0.86 mmol) in 3 mL of anhydrous DMF was added the title A compound (334 mg, 1.29 mmol) at room temperature. The reaction mixture was stirred for 6 h then a second 334 mg portion of the title A compound was added. After an additional 18 h a third 334 mg portion of the title A compound was added. The mixture was stirred for 6 h then diluted with 25 mL of ethyl acetate, washed with three-25 mL portions of 1M aq NaOH solution, dried (sodium sulfate) and concentrated in vacuo to give an oil. The crude oil was purified by flash chromatography (Merck silica, 18×3.0 cm, 1:14 methanol/methylene chloride) to afford the title compound as a solid white foam (128 mg, 0.27 mmol, 32%).

Workup

  1. additiona second 334 mg portion of the title A compound was added
  2. stirringThe mixture was stirred for 6 h
  3. washwashed with three-25 mL portions of 1M aq NaOH solution
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThe crude oil was purified by flash chromatography (Merck silica, 18×3.0 cm, 1:14 methanol/methylene chloride)

Sources & evidence

ORD record
ord-9ac7b21ae2ed411795130e081b258e93
Source dataset
uspto-grants-1997_03
Patent number
US05612323

Reaction notes

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