1-Hydroxybenzotriazole → HCID 68426021, compound

HRID 1157186Notes

Reaction equation

HRID 1157186 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[C:43]([Cl:48])[CH:42]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[CH2:8][N:9]1[CH2:13][CH2:12][CH:11]([C:14](=[O:16])[NH:40][C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[C:43]([Cl:48])[CH:42]=2)[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 775784-Amino-2-chlorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3028194LithiumHCID 674198661823466-92-7

Product 1

HCID 68426021HCID 68426021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-tert-Butoxycarbonylmethyl-pyrrolidine-3-carboxylic acid, Lithium salt (0.5 g, 2.12 mmol) and HOBt (0.45 g, 3.3 mmol) in DMF (10 ml) at 0° C. was added EDCl (630 mg, 3.3 mmol). The formed reaction mixture was stirred at 0° C. for 0.5 hour and then 4-amino-2-chloro-phenol was added. After stirred at RT for overnight, the reaction mixture was added to ice-water (50 g) and the formed precipitated was collected by filtration, washed with sodium bicarbonate and HCl (0.1 N). After drying in air, the crude product (720 mg) was used directly in the next step. Mass Spec ES (355.2, M+H)

Workup

  1. customThe formed reaction mixture
  2. stirringAfter stirred at RT for overnight
  3. customthe formed precipitated
  4. filtrationwas collected by filtration
  5. washwashed with sodium bicarbonate and HCl (0.1 N)
  6. customAfter drying in air

Sources & evidence

ORD record
ord-5bc2c1a1e7ea4b37aa3678c185eac645
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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