1-Bromo-2-methylpropane → (4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine

HRID 276480Notes

Reaction equation

HRID 276480 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]=[C:12]3[NH:16][C@@H:15]([CH:17]([CH2:19][CH3:20])[CH3:18])[CH2:14][S:13]3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH2:21](Br)[CH:22]([CH3:24])[CH3:23]>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]=[C:12]3[N:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C@@H:15]([CH:17]([CH2:19][CH3:20])[CH3:18])[CH2:14][S:13]3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 65551-Bromo-2-methylpropaneHCID 178445838(4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-1,3-thiazolidine

Product 1

HCID 59113177(4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine

Procedure

(1S)-1-(Hydroxymethyl)-2-methylbutylamine was made from (L)-isoleucine methyl ester as described in Method B1b. The 2-hydroxyethylamine was converted to (1S)-1-(chloromethyl)-2-methylbutanammonium chloride as described in Method B7a. 5-Aminoindan-1-one was converted to 1-oxo-5-indanyl isothiocyanate according to Method A2a. The isothiocyanate was reacted with (1S)-1-(chloromethyl)-2-methylbutanammonium chloride to Method C1a to give (4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(1-oxo-5-indanylimino)-4-(2-butyl)-3-isobutyl-1,3-thiazolidine.

Sources & evidence

ORD record
ord-327bb24bc37b4a298de6954827046de9
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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