Hydrazine hydrate (1:1) → HCID 59091451, compound

HRID 1242108Notes

Reaction equation

HRID 1242108 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([CH2:17][N:18]3C(=O)C4C(=CC=CC=4)C3=O)[N:13]([C@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:30])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][C@@H:14]([CH2:17][NH2:18])[N:13]([C@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:30])[CH2:12][C:11]=2[S:10][C:9]=1[NH2:37])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21060909HCID 21060909, compound

Product 1

HCID 59091451HCID 59091451, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-5-(S)-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-6-(1-(S)-phenyl-ethyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic-acid tert-butyl ester (7.96 g, 15.4 mmol) and hydrazine hydrate (3.85 g, 77.0 mmol) in ethanol (250 ml) was stirred for 16 hours at room temperature. The solvent was removed in vacuo and the solid residue was extracted with diethyl ether (3×200 ml). The fractions were combined and the solvent removed in vacuo to give 5.9 g (100%) of 2-amino-5-(S)-aminomethyl-6-(1-(S)-phenyl-ethyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe solid residue was extracted with diethyl ether (3×200 ml)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-564cad6348d84570a33afabd8388b919
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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