Ammonium Hydroxide → Boc-Ala-NH2

HRID 216301Notes

Reaction equation

HRID 216301 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[N:16]=C=NCCCN(C)C.ON1C(=O)CCC1=O.[OH-].[NH4+]>O1CCCC1.CN(C)C=O>[NH2:16][C:11](=[O:13])[C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH3:10]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 7015295Boc-Ala-NH2Yield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing Boc-L-alanine (1.0 g, 5.29 mmol) in a mixture of tetrahydrofuran (25 mL) and N,N-dimethylformamide (5 mL) were added EDAC (1.5 g, 7.82 mmol) and N-hydroxysuccinimide (0.91 g, 7.91 mmol) and the mixture was stirred at room temperature for 16 hours. Aqueous ammonium hydroxide solution (15 mL, 28%) was added and the mixture was stirred for 0.5 hours at room temperature. The reaction was partitioned between ethyl acetate and water, and the organic was washed with brine and dried over MgSO4, filtered and evaporated to give the product (0.483 g, 49% yield), which was used without further purification.

Workup

  1. stirringthe mixture was stirred for 0.5 hours at room temperature
  2. customThe reaction was partitioned between ethyl acetate and water
  3. washthe organic was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-da9034ffadd44ec8af2de9ac131a2850
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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