Hydrochloric Acid → Ammonium Hydroxide

HRID 1367235Notes

Reaction equation

HRID 1367235 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-f423c372f145486ba62a7e92895fdb76
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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