Methanol → HCID 68155913, compound

HRID 1877811Notes

Reaction equation

HRID 1877811 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([CH3:26])([CH3:25])[C:22]([OH:24])=[O:23])[CH2:16][CH2:15]3)[C:11]3=[CH:27][C:28]([CH2:30][CH3:31])=[CH:29][N:10]3[CH2:9][C:8]=2[CH:32]=1.CO>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:21]([CH3:26])([CH3:25])[C:22]([OH:24])=[O:23])[CH2:18][CH2:19]3)[C:11]3=[CH:27][C:28]([CH2:30][CH3:31])=[CH:29][N:10]3[CH2:9][C:8]=2[CH:32]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 68156146HCID 68156146, compound

Product 1

HCID 68155913HCID 68155913, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dissolve 3-[4-(7-chloro-2-ethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride (201 mg, 400 μmoles in water and methanol (5 mL) then load on to a SCX-2 cartridge (2 g). Wash with methanol and then elute with ammonia in methanol. Concentrate the basic solution to dryness to give 3-[4-(7-chloro-2-ethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid (160 mg, 373 μmoles). Then treat with 2N sodium hydroxide (187 μL, (373 μmoles) and water (3 mL) to cause solution. Then freeze-dry to yield sodium 3-[4-(7-chloro-2-ethyl-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoate (164 mg, 98% yield). MS (m/z): 429.18 (M+1).

Workup

  1. washWash with methanol
  2. washelute with ammonia in methanol
  3. concentrationConcentrate the basic solution to dryness

Sources & evidence

ORD record
ord-63ce8a1374604b59b26134aca00a3af1
Source dataset
uspto-grants-2012_11
Patent number
US08314092B2

Reaction notes

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