1-Hydroxybenzotriazole → HCID 22645338, compound

HRID 2414683Notes

Reaction equation

HRID 2414683 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1.Cl.C(N=C=NCCCN(C)C)C>>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([O:12][N:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[N:17]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 22645338HCID 22645338, compoundYield 91.9%

Procedure

To a solution of 2-tert-butoxycarbonylamino-2-methylpropionic acid (2.03 g) and 1-hydroxybenzotriazole (1.35 g) in N,N-dimethylfolmamide (20 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.91 g) and the mixture was stirred overnight. The reaction mixture was partitioned between a mixture of ethyl acetate and n-hexane and water. The separated organic layer was washed in turn with water, a saturated sodium hydrogencarbonate in water and brine and dried over magnesium sulfate. The organic layer was evaporated under reduced pressure to give benzotriazol-1-yl 2-tert-butoxycarbonylamino-2-methylpropionate (2.94 g, 91.9%) as a solid.

Workup

  1. customThe reaction mixture was partitioned between a mixture of ethyl acetate and n-hexane and water
  2. washThe separated organic layer was washed in turn with water
  3. dry with materiala saturated sodium hydrogencarbonate in water and brine and dried over magnesium sulfate
  4. customThe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7118b2d19fe44928be44f6b8407b5e79
Source dataset
uspto-grants-2004_11
Patent number
US06812235B2

Reaction notes

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