Triethylamine → ethyl (S)-4-[[1-(aminocarbonyl)propyl]amino]butyrate

HRID 2309724Notes

Reaction equation

HRID 2309724 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12].Br[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C1(C)C=CC=CC=1>[NH2:13][C:11]([C@@H:10]([NH:9][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76300Ethyl 4-bromobutyrateHCID 11961924(2S)-2-Aminobutanamide hydrochloride

Product 1

HCID 29938336ethyl (S)-4-[[1-(aminocarbonyl)propyl]amino]butyrate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

143.6 ml (1.035 mole) of triethylamine are added to a suspension of 47.75 g (0.345 mole) of (S)-2-amino-butanamide hydrochloride ([alpha]D25 : +26.1°; c=1, methanol) in 400 ml of toluene. The mixture is heated to 80° C. and 67.2 g (0.345 mole) of ethyl 4-bromobutyrate are introduced dropwise.

Sources & evidence

ORD record
ord-79b3e9246e9248dfb84d77acd5058582
Source dataset
uspto-grants-1987_09
Patent number
US04696943

Reaction notes

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