1-Bromo-2-methylpropane → HCID 22951240, compound

HRID 276284Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[NH:16][C@@H:15]([C@H:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:18])[CH2:14][S:13]1.[CH2:24](Br)[CH:25]([CH3:27])[CH3:26]>>[C:20]([O:19][C@@H:17]([C@H:15]1[CH2:14][S:13][C:12](=[N:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[N:16]1[CH2:24][CH:25]([CH3:27])[CH3:26])[CH3:18])([CH3:22])([CH3:21])[CH3:23]

Participants

Reactant 2

HCID 65551-Bromo-2-methylpropane

HCID 178428757HCID 178428757, compound

Product 1

HCID 22951240HCID 22951240, compoundYield 56%

Procedure

(1R,2R)-1-(Methanesulfonyloxymethyl)-2-(tert-butoxy)propanammonium chloride (Method B8a; 1.5 g, 5.5 mmol) was reacted with 2-methyl-4-nitrophenyl isothiocyanate in a manner analogous to that described in Method C1a to afford 4(S)-(1(R)-tert-butoxyethyl)-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine (1.2 g, 67%). The (4S)-2-(2-methyl-4-nitrophenylimino)-4-(1(R)-tert-butoxyethyl)-1,3-thiazolidine was reacted with isobutyl bromide in a manner analogous to Method D2a to yield (4S)-4-(1(R)-tert-butoxyethyl)-3-isobutyl-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine (0.26 g, 56%): TLC (25% EtOAc/hex) Rf0.67.

Sources & evidence

ORD record: ord-8c17090c93fe4b95b849c116c693a280
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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