Water → HCID 57551817, compound

HRID 907295Notes

Reaction equation

HRID 907295 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4C=O)[CH:7]=2)[CH2:3][CH2:2]1.C[C@H:32]1[CH2:37][NH:36][CH2:35][CH2:34][N:33]1[C:38](OC(C)(C)C)=O.[C:45](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[CH:1]1([NH:4][C:5](=[O:30])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[CH:17]=[C:16]4[CH2:38][N:33]3[CH2:32][CH2:37][NH:36][C@@H:35]([CH3:45])[CH2:34]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 57551737HCID 57551737, compound

Product 1

HCID 57551817HCID 57551817, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of Example 59 step iii) (0.25 g), (S)-2-methylpiperazine-1-carboxylic acid, tert-butyl ester (0.37 g) and sodium triacetoxyborohydride (0.40 g) were stirred in dichloromethane (20 mL) under nitrogen for 16 hours. Water (20 mL) and dichloromethane (20 mL) were then added and the organics separated. The organics were evaporated under reduced pressure. The residue was dissolved in methanol (5 mL) and 4M HCl in 1,4-dioxane (2 mL) added. The mixture was stirred overnight at room temperature. The volatiles were removed under vacuum and the residue purified by HPLC to give the title compound as a solid (0.11 g).

Workup

  1. customThe organics were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (5 mL)
  3. addition4M HCl in 1,4-dioxane (2 mL) added
  4. customThe volatiles were removed under vacuum
  5. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-b054b063a5444442bce513fc2b2b1b75
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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