L-Alanine → Boc-Asn-Ala-OBzl

HRID 1703833Notes

Reaction equation

HRID 1703833 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][C:11](=[O:13])[NH2:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:17][C:18]1[CH:19]=[CH:20][C:21](S(O)(=O)=O)=[CH:22][CH:23]=1.[NH2:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30].CN1CCOCC1>CN(C)C=O>[NH:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[C@H:9]([C:14]([NH:28][C@H:29]([C:31]([O:33][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:32])[CH3:30])=[O:16])[CH2:10][C:11](=[O:13])[NH2:12]

Participants

6

Reactant 4

HCID 5950L-AlanineHCID 6101p-Toluenesulfonic acidHCID 79724-MethylmorpholineHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

Product 1

HCID 131711194Boc-Asn-Ala-OBzlYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (4.24 mmoles) of p-nitrophenyl ester of BOC-Asparagine are added to a solution cooled to 0° of 1.7 g (4.84 mmoles) of p-toluene sulfonate of the benzyl ester of alanine and of 0.53 ml (4.84 mmoles) of N-methylmorpholine, in 15 ml of dimethylformamide. After 24 hours at ambiant temperature, the product is purified as described above. In suspension in ether, 1.33 g (79%) of the product is obtained after filtration, having a melting point and a rotatory power (in dimethyl formamide) respectively of m.p. 138°-141°; αD25 = 17.5° (c = 1.02 DMF).

Workup

  1. customthe product is purified

Sources & evidence

ORD record
ord-bb7371a49f9a40e586a8b1c4c84cb7f0
Source dataset
uspto-grants-1978_11
Patent number
US04125606

Reaction notes

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