1-Hydroxybenzotriazole → HCID 70047443, compound

HRID 977018Notes

Reaction equation

HRID 977018 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]([O:17][C:18]([CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:25](O)=[O:26])=[O:19])([CH3:16])([CH3:15])[CH3:14].C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[C:59]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)(=[O:62])[NH:60][NH2:61]>CN(C=O)C>[C:13]([O:17][C:18]([CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:25]([NH:61][NH:60][C:59]([O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)=[O:62])=[O:26])=[O:19])([CH3:15])([CH3:16])[CH3:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19610505HCID 19610505, compound

Product 1

HCID 70047443HCID 70047443, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g) was added to a mixture of the product of step (c) (3.82 g), HOBT (1.71 g), diisopropylethylamine (1.75 ml) and DMF (30 ml) at ambient temperature and stirred for 30 minutes. Benzyl carbazate (1.66 g) in DMF (10 ml) was added and the mixture was stirred for 20 hours at ambient temperature. The solvent was removed by evaporation. The residue was dissolved in ethyl acetate (160 ml) and the solution was washed with 1M citric acid solution (25 ml), water (2×25 ml), 1M sodium hydroxide solution (20 ml), water (25 ml) and with saturated sodium chloride solution (25 ml) and dried (MgSO4). The solvent was removed by evaporation to give benzyl 3-(3,4-di-t-butoxycarbonylmethoxybenzoyl)carbazate as a gum; NMR Spectrum (d6 -DMSO) 1.43 (s, 18H), 4.70 (s, 2H), 4.75 (s, 2H), 5.11 (s, 2H), 6.96 (d, 1H), 7.34 (br s, 5H), 7.4 (d, 1H), 7.49 (dd, 1H), 9.28 (br s, 1H), 10.17 (br s, 1H); Mass Spectrum (+ve FAB, DMSO/GLYCEROL) 530 (M+H)+.

Workup

  1. stirringthe mixture was stirred for 20 hours at ambient temperature
  2. customThe solvent was removed by evaporation
  3. dissolutionThe residue was dissolved in ethyl acetate (160 ml)
  4. washthe solution was washed with 1M citric acid solution (25 ml), water (2×25 ml), 1M sodium hydroxide solution (20 ml), water (25 ml) and with saturated sodium chloride solution (25 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-01c9372de5c14b58be6aea372fade6d3
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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