1-Hydroxybenzotriazole → HCID 10787454, compound

HRID 322923Notes

Reaction equation

HRID 322923 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[CH:14][C:10]=1[C:11]([NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9840634HCID 9840634, compound

Product 1

HCID 10787454HCID 10787454, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2,4-dibenzyloxybenzoic acid (3.34 g) and methyl glycinate hydrochloride (1.25 g) in DMF (40 mL) is treated with triethylamine (2.23 g) and 1-hydroxybenzotriazole (1.53 g) at 0° C. The mixture is stirred for 10 minutes, treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (2.05 g) and allowed to warm to 25° C. The solution is evaporated. The residue is partitioned between ethyl acetate and water. The organic layer is washed with 1 M HCl, 1 M NaOH, water, dried and evaporated. The residue is recrystallized from methanol to yield methyl N-(2,4-dibenzyloxybenzoyl)glycinate as a solid (900 mg). H NMR (CDCl3) 3.7(3H,s), 4.2(2H,d), 5.1 (2H,s), 5.2(2H,s), 6.6(1H,s), 6.7(1H,d), 7.3-7.5(10H,m), 8.2(1H,d), 8.4(1H,t).

Workup

  1. customThe solution is evaporated
  2. customThe residue is partitioned between ethyl acetate and water
  3. washThe organic layer is washed with 1 M HCl, 1 M NaOH, water
  4. customdried
  5. customevaporated
  6. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-2c03ddf6f4c6452da9492df635a38ddf
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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