1-Hydroxybenzotriazole → HCID 76542821, compound

HRID 1361003Notes

Reaction equation

HRID 1361003 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])=[CH:11][CH:10]=2)[S:3]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:48]([O:52][C:53](=[O:59])[NH:54][CH2:55][CH2:56][CH2:57][NH2:58])([CH3:51])([CH3:50])[CH3:49]>CN(C=O)C>[C:48]([O:52][C:53](=[O:59])[NH:54][CH2:55][CH2:56][CH2:57][NH:58][C:23](=[O:24])[CH2:22][CH2:21][CH2:20][O:19][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([CH:8]=[C:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])=[CH:10][CH:11]=1)([CH3:51])([CH3:49])[CH3:50]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 76542804HCID 76542804, compound

Product 1

HCID 76542821HCID 76542821, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)naphthalen-1-yloxy]butyric acid (example 291, 5.9 g, 16.5 mmol) and 1-hydroxybenzotriazole (3.35 g, 24.8 mmol) in DMF (60 mL) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (4.75 g, 24.8 mmol) and the resulting mixture was stirred at room temperature for 2 hours. N-(3-aminopropylcarbamic acid tert-butyl ester (3.45 g, 19.8 mmol) was added and the resulting mixture was stirred at room temperature for 16 hours. The mixture was concentrated in vacuo and ethyl acetate and dichloromethane were added to the residue. The mixture was filtered, washed with water and dried in vacuo to afford 4.98 g (59%) of (3-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)naphthalen-1-yloxy]butyrylamino}propyl)carbamic acid tert-butyl ester.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 16 hours
  2. concentrationThe mixture was concentrated in vacuo and ethyl acetate and dichloromethane
  3. additionwere added to the residue
  4. filtrationThe mixture was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-606f0e9cda5f44c19511f42ca4d65abe
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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