Z-Dap-OH → (S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

HRID 1759714Notes

Reaction equation

HRID 1759714 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:15]([OH:17])=[O:16])[NH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]>C(OC(C)(C)C)(=O)C>[NH2:1][CH2:2][C@@H:3]([C:15]([O:17][C:9]([CH3:14])([CH3:10])[CH3:8])=[O:16])[NH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

3

Reactant 1

HCID 2756313Z-Dap-OH

Product 1

HCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

2.5 ml of concentrated HClO4 is added without exceeding 5° C. to a suspension of 5 g of N-alpha-[(phenylmethoxy)carbonyl]-L-alpha,beta-diaminopropionic acid 10-1 (alternative nomenclature: (3-amino-N-[(phenylmethoxy)carbonyl]-L-alanine) in 25 ml of tertbutyl acetate cooled down to 0° C., the temperature of the reaction medium is allowed to rise to 20° C. and agitation is carried out for 4 days at 20° C. The reaction medium is poured into a sodium bicarbonate/ice solution (300 ml/200 ml), followed by extracting with ethyl acetate, filtering, decanting, drying the organic phase, evaporating under reduced pressure until a dry extract is obtained corresponding to the expected product (3.2 g) which is used as it is in the following reaction.

Workup

  1. customto rise to 20° C.
  2. extractionby extracting with ethyl acetate
  3. filtrationfiltering
  4. customdecanting
  5. customdrying the organic phase
  6. customevaporating under reduced pressure until a dry
  7. extractionextract

Sources & evidence

ORD record
ord-61ba45302fca4d32ad0f66e13bea2a06
Source dataset
uspto-grants-2005_01
Patent number
US06838453B2

Reaction notes

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