Hydrochloric Acid → Ammonium Hydroxide

HRID 1866714Notes

Reaction equation

HRID 1866714 reaction equation
Cl.C([S@@]([NH:8][C@H:9]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=1)[CH2:10][CH2:11][C@@:12]1([C:27]([O:29]C)=O)[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:7])(C)(C)C.C(N(CC)CC)C>CO>[NH4+:8].[OH-:7].[F:38][C:33]1[CH:32]=[C:31]([C@@H:9]2[CH2:10][CH2:11][C@@:12]3([N:13]([C:17]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[O:18])[CH2:14][CH2:15][CH2:16]3)[C:27](=[O:29])[NH:8]2)[CH:36]=[C:35]([F:37])[CH:34]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 866257451-Benzyl 2-methyl (2R)-2-[(3S)-3-{[(S)-tert-butylsulfinyl]amino}-3-(3,5-difluorophenyl)propyl]pyrrolidine-1,2-dicarboxylate

Product 2

HCID 14923Ammonium HydroxideHCID 66973302HCID 66973302, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (g) was bubbled through a solution of 1-benzyl 2-methyl (2R)-2-[(3S)-3-{[(S)-tert-butylsulfinyl]amino}-3-(3,5-difluorophenyl)propyl]pyrrolidine-1,2-dicarboxylate from Step C (1.02 g, 1.90 mmol) in MeOH (25 mL) at 0° C. for 1 min. After stirring for 1 h, the reaction mixture was concentrated to dryness in vacuo. To the crude product suspended in toluene (25 mL) was added triethylamine (2.12 mL, 15.2 mmol), and the reaction mixture was heated to reflux for 66 h. The reaction mixture was concentrated in vacuo and the crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 95:5:1, to give the title compound. MS: m/z=401 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 66 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-19d47a0f717c429da06d9e2263423609
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

Loading…