Hydrazine hydrate (1:1) → HCID 86756741, compound

HRID 1978076Notes

Reaction equation

HRID 1978076 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:22]([NH:24][N:25]([S:39]([CH3:42])(=[O:41])=[O:40])[CH2:26][CH2:27][N:28]1C(=O)C2=CC=CC=C2C1=O)=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].O.NN>CO>[NH2:28][CH2:27][CH2:26][N:25]([S:39]([CH3:42])(=[O:41])=[O:40])[NH:24][C:22](=[O:23])[C@@H:21]([C@@H:11]([C:9](=[O:10])[NH:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:43][CH:44]([CH3:46])[CH3:45]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86756742HCID 86756742, compound

Product 1

HCID 86756741HCID 86756741, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 0.926 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(methanesulphonyl)-4-methyl-2′-(2-phthalimidoethyl)valerohydrazide in 10 ml of methanol was treated with 0.25 ml of hydrazine hydrate. The mixture was stirred at room temperature overnight. The suspended white solid was filtered off, the filtrate was concentrated and the residue was purified by chromatography on silica gel using 5% methanol in dichloromethane for the elution. There was obtained 0.23 g of (E)-2′-(2-aminoethyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl)-4-phenyl-3-butenyl]-2′-(methanesulphonyl)-4-methylvalerohydrazide in the form of a white solid after trituration of the product with ether.

Workup

  1. filtrationThe suspended white solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by chromatography on silica gel using 5% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-2bc5c69e5c29420594a36127469efac8
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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