HCID 11267230, compound → HCID 67902065, compound

HRID 1249292Notes

Reaction equation

HRID 1249292 reaction equation
[N+:1](=[CH:3][CH:4]([CH3:6])[CH3:5])=[N-:2].[N+:7]([C:10]1[CH:29]=[CH:28][C:13]([CH2:14][O:15][C:16](=[O:27])[C:17](=[CH2:26])[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][CH:11]=1)([O-:9])=[O:8]>C(Cl)Cl>[C:22]([O:21][C:19]([NH:18][C:17]1([C:16]([O:15][CH2:14][C:13]2[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:29][CH:28]=2)=[O:27])[CH2:26][CH:3]([CH:4]([CH3:6])[CH3:5])[NH:1][NH:2]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 11267230HCID 11267230, compoundHCID 12511037HCID 12511037, compound

Product 1

HCID 67902065HCID 67902065, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ethereal diazoisobutane (6) was gradually added to a solution of Boc-dehydroalanine-p-nitrobenzyl ester (2) (967 mg, 3 mmol) in CH2Cl2 (15 ml) at -10° C. to -15° C. with stirring. After stirring for 1 hr at the same temperature, the solvent was evaporated in vacuo and the resulting residue was triturated with hexane and filtered by suction to give 1.2 g of p-nitrobenzyl p-nitrobenzyl 3-t-butoxycarbonylamino-5-isopropylpyrazoline-3-carboxylate (7) (98.4%) mp 78°-79° C. (dec.). Recrystallization from AcOEt-n hexane gave colorless prisms having mp 87°-89° C. (dec.); IR (KBr) 3390(NH), 1745(C=O), 1690(C=O), 1605 (N=N).NMR (CDCl3)δ: 8.2 and 7.5 (d, d, 4H, ArH), 6.2 (br s, 1H, NH); 5.30 (s, 2H, OCH2), 4.8-5.2 (m, 1H, CH--N=N), 1.5-2.3 (m, 3H, (CH3)2CH and CH2), 1.35 (s, 9H, Boc), 1.00-1.30 (m, 3H, CH3), 0.8-1.10 (m, 3H, CH3).

Workup

  1. stirringAfter stirring for 1 hr at the same temperature
  2. customthe solvent was evaporated in vacuo
  3. customthe resulting residue was triturated with hexane
  4. filtrationfiltered by suction

Sources & evidence

ORD record
ord-c4924c102eae4d5ca90d2bd22735ced3
Source dataset
uspto-grants-1986_12
Patent number
US04629784

Reaction notes

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