Hydrazine → HCID 86638997, compound

HRID 656230Notes

Reaction equation

HRID 656230 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[C@H:11]([S:19]C(=O)C2C=CC=CC=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[C@H:11]([SH:19])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86638998HCID 86638998, compound

Product 1

HCID 86638997HCID 86638997, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of thiobenzoic acid S-((6R,8R)-8-tert-butoxycarbonylamino-1,4-dioxa-spiro[4.5]dec-6-yl) ester+(6S,8S) diastereomer (695 mg, 1.77 mmol) and hydrazine (80% aq. solution, 0.10 ml, 2.65 mmol) in 7 ml of dichloromethane was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with 1M aqueous HCl, dried and stripped of the solvent to obtain the title compound (490 mg, 95% yield) as yellow-gray oil.

Workup

  1. washwashed with 1M aqueous HCl
  2. customdried

Sources & evidence

ORD record
ord-bfb23101ea754618a92041fdb2627a3d
Source dataset
uspto-grants-2011_12
Patent number
US08071643B2

Reaction notes

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