Potassium bisulfate → HCID 68431995, compound

HRID 1867452Notes

Reaction equation

HRID 1867452 reaction equation
C[O:2][C:3](=O)[CH:4]([N:14]1[C:20](=[O:21])[CH2:19][CH2:18][N:17]([C:22](=[O:33])/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:16][CH2:15]1)[CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[BH4-].[Na+].OS([O-])(=O)=O.[K+]>C(O)C>[Cl:32][C:27]1[CH:26]=[C:25](/[CH:24]=[CH:23]/[C:22]([N:17]2[CH2:18][CH2:19][C:20](=[O:21])[N:14]([CH:4]([CH2:3][OH:2])[CH2:5][CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:15][CH2:16]2)=[O:33])[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 4311764Sodium borohydride2×HCID 68432142HCID 68432142, compound

Product 1

HCID 68431995HCID 68431995, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 0.041 g (0.08 mmol) of (rac)-2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-5-piperidin-1-yl-pentanoic acid methyl ester in 0.5 ml of ethanol was treated at 0° C. with 0.006 g (0.16 mmol) of sodium borohydride in 0.5 ml of ethanol during 5 min. The reaction was stirred for 21 h at RT, cooled (0° C.) and treated again with 0.006 g (0.16 mmol) of sodium borohydride in 0.5 ml ethanol. After 5 h at RT the reaction was neutralized with cold aqueous 10% KHSO4 and extracted with cold saturated NaHCO3/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4, evaporated and purified by flash silica gel column (CH2Cl2/MeOH 9:1 to 4:1 and then, to elute the product, with CH2Cl2/MeOH/25% NH4OH 9:1:0.1) to yield after precipitation with CH2Cl2/n-penatne 0.022 g (57%) of the title compound as white foam. MS: 482.3 (MH+, 2Cl).

Workup

  1. temperaturecooled (0° C.)
  2. extractionextracted with cold saturated NaHCO3/EtOAc (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (CH2Cl2/MeOH 9:1 to 4:1
  7. washto elute the product
  8. customwith CH2Cl2/MeOH/25% NH4OH 9:1:0.1) to yield
  9. customafter precipitation with CH2Cl2/n-penatne 0.022 g (57%) of the title compound as white foam

Sources & evidence

ORD record
ord-c2b321095ba3458ca4c5f54e26529561
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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