Hydrazine hydrate (1:1) → HCID 66916874, compound

HRID 2281592Notes

Reaction equation

HRID 2281592 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([CH2:24][N:25]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([CH3:4])([CH3:3])[CH3:2].O.NN>C(Cl)Cl.CCO>[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([CH2:24][NH2:25])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67087202HCID 67087202, compound

Product 1

HCID 66916874HCID 66916874, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [(S)-5-benzyloxycarbonylamino-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-pentyl]-carbamic acid tert-butyl ester (0.63 g, 1.27 mmol) in DCM (5.1 ml) and EtOH (5.1 ml) is treated with hydrazine hydrate (0.318 g, 6.35 mmol) and the reaction mixture is stirred at room temperature overnight. A white precipitate forms which is removed by filtration and washed with DCM (3×10 ml). The filtrate is concentrated in vacuo and redissolved in DCM (15 ml) and MeOH (2 ml). Undissolved material is removed by filtration and the filtrate is concentrated in vacuo. The resulting oily yellow solid is purified by chromatography on silica eluting with 10-50% MeOH in DCM (1% TEA) to afford ((S)-1-Aminomethyl-5-benzyloxycarbonylamino-pentyl)-carbamic acid tert-butyl ester as a clear oil; [M+H]+ 366

Workup

  1. customA white precipitate forms which is removed by filtration
  2. washwashed with DCM (3×10 ml)
  3. concentrationThe filtrate is concentrated in vacuo
  4. dissolutionredissolved in DCM (15 ml)
  5. customUndissolved material is removed by filtration
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe resulting oily yellow solid is purified by chromatography on silica eluting with 10-50% MeOH in DCM (1% TEA)

Sources & evidence

ORD record
ord-efd1941388ed44fd93c3abd5a3735e25
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

Loading…