Hydrochloric Acid → HCID 11995991, compound

HRID 1948330Notes

Reaction equation

HRID 1948330 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:27]([O:29]CC)=[O:28])=[C:21]([C:23]([NH:25][CH3:26])=[O:24])[N:22]=2)[CH2:14][C@@H:13]1[O:32][CH3:33])=[O:10].[OH-].[Ba+2].[OH-].O.Cl>CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:27]([OH:29])=[O:28])=[C:21]([C:23]([NH:25][CH3:26])=[O:24])[N:22]=2)[CH2:14][C@@H:13]1[O:32][CH3:33])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6093286Barium hydroxideHCID 68519250HCID 68519250, compound

Product 1

HCID 11995991HCID 11995991, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension/solution of ethyl 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-[(methylamino)carbonyl]-1,3-thiazole-5-carboxylate (0.078 g, 0.15 mmol, Example 218) in methanol (2 mL) was added barium hydroxide (0.052 g, 0.30 mmol) and water (0.5 mL). After stirring several hours the reaction was complete. The reaction was acidified with 1N HCl and then concentrated to remove methanol. The residue was extracted with EtOAc (×3), dried with MgSO4 and concentrated to a white solid (0.059 g). MS (ES) M+H+: 490 for C18H21Cl2N5O5S; NMR: 1.76 (s, 2 H) 2.18 (s, 3 H) 2.86 (s, 3 H) 3.38 (s, 3 H) 3.56 (s, 2 H) 4.02 (s, 1 H) 4.27 (s, 2 H) 4.40 (s, 1 H) 7.15 (s, 1 H) 9.38 (s, 1 H) 12.15 (s, 1 H).

Workup

  1. concentrationconcentrated
  2. customto remove methanol
  3. extractionThe residue was extracted with EtOAc (×3)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated to a white solid (0.059 g)

Sources & evidence

ORD record
ord-4d9e1518a85a46c09301875ae2c49a7a
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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