Phosgene → HCID 86756951, compound

HRID 1979242Notes

Reaction equation

HRID 1979242 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:13](Cl)(Cl)=[O:14].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][NH:24][C:25]([C@H:27]([C@@H:37]([CH2:46][CH:47]([CH3:49])[CH3:48])[C:38]([NH:40][NH:41][CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26]>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.ClCCl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][NH:24][C:25]([C@H:27]([C@@H:37]([CH2:46][CH:47]([CH3:49])[CH3:48])[C:38]([NH:40][N:41]([CH2:42][CH:43]([CH3:44])[CH3:45])[C:13]([N:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:14])=[O:39])[CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:26]

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 21857793tert-Butyl pyrazolidine-1-carboxylateHCID 86756879(E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)-carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756951HCID 86756951, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 21877217Toluene methylene chlorideSolvent

Procedure

A solution of 0.241 g of 2-tert.butyloxycarbonyl-pyrazolidine in 5 ml of toluene as added slowly, at 0° C. under nitrogen, to a solution of 0.725 ml of phosgene in 5 ml of toluene. The mixture was allowed to warm to room temperature over 2 hours and then a solution of 0.459 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5ml toluene/dichloromethane (1:1) was added dropwise. The mixture was stirred for 48 hours at room temperature and evaporated. The residue was dissolved in ethyl acetate and washed with 2N aqueous hydrogen chloride and water and then dried over anhydrous magnesium sulphate and evaporated. The residue was triturated with ether to give 0.267 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-[(2-tert.butyloxycarbonyl-1-pyrazolidinyl)carbonyl]valerohydrazide in the form of a pale yellow solid.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 2N aqueous hydrogen chloride and water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-44fbfac69b814e76bf1b4a49b82ef23b
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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