Triethylamine → HCID 86739547, compound

HRID 1462483Notes

Reaction equation

HRID 1462483 reaction equation
Cl[P:2]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:6])[O:3][CH2:4][CH3:5].[NH2:17][CH:18]1[CH2:23][S:22][C@H:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:19]1=[O:36].C(N(CC)CC)C>C(Cl)Cl>[CH2:4]([O:3][P:2]([NH:17][CH:18]1[CH2:23][S:22][C@H:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:19]1=[O:36])([CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15591238Ethoxy(4-phenylbutyl)phosphinyl chlorideHCID 86739548HCID 86739548, compound

Product 1

HCID 86739547HCID 86739547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the crude chloro(4-phenylbutyl)phosphinic acid, ethyl ester (2.6 mmole), dry methylene chloride (9.0 ml.) and (R)-dihydro-5-amino-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, ethyl ester (0.72 g., 2.4 mmole) at 0° (ice bath) in an argon atmosphere is treated dropwise with triethylamine (0.44 ml., 1.3 eq.) in methylene chloride (2 ml.) over 5 minutes. After 30 minutes, the ice bath is removed and the reaction mixture is stirred at room temperature for 16 hours. The mixture is diluted with ethyl acetate and washed successively with saturated sodium bicarbonate, 5% potassium bisulfate, brine, dried (MgSO4), and evaporated. The residue (1.5 g.) is chromatographed on silica (80 g.) eluting with hexane/acetone (2:1) to give 1.0 g. of (R)-dihydro-5-[[ethoxy(4-phenylbutyl)phosphinyl]amino]-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, ethyl ester as an oil after evaporation. TLC (hexane/acetone, 2:1) single spot at Rf =0.5.

Workup

  1. customthe ice bath is removed
  2. additionThe mixture is diluted with ethyl acetate
  3. washwashed successively with saturated sodium bicarbonate, 5% potassium bisulfate, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue (1.5 g.) is chromatographed on silica (80 g.)
  7. washeluting with hexane/acetone (2:1)
  8. customto give 1.0 g
  9. customof (R)-dihydro-5-[[ethoxy(4-phenylbutyl)phosphinyl]amino]-4-oxo-2-phenyl-2H-1,3-thiazine-3(4H)-acetic acid, ethyl ester as an oil after evaporation

Sources & evidence

ORD record
ord-49adfe41884a4ac28720f7632f38b268
Source dataset
uspto-grants-1984_07
Patent number
US04460579

Reaction notes

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