Carbamate → HCID 22951244, compound

HRID 276475Notes

Reaction equation

HRID 276475 reaction equation
[C:1]([O:5][NH:6][C:7]([NH:9][C@H:10]([C:15](O)=[O:16])[C@@H:11]([CH2:13][CH3:14])[CH3:12])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])N.[CH3:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[N:32]=[C:33]=[S:34]>>[C:1]([O:5][NH:6][C:7]([NH:9][C@H:10]([CH2:15][OH:16])[C@H:11]([CH3:12])[CH2:13][CH3:14])=[O:8])([CH3:3])([CH3:4])[CH3:2].[CH3:22][C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[CH:26]=[CH:25][C:24]=1[N:32]=[C:33]1[NH:9][C@@H:10]([C@@H:11]([CH2:13][CH3:14])[CH3:12])[CH2:15][S:34]1

Participants

5

Reactant 3

HCID 276CarbamateHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 22951245HCID 22951245, compound

Product 2

HCID 22951244HCID 22951244, compoundHCID 178455882HCID 178455882, compound

Procedure

N-(tert-Butoxycarbamoyl)-(1S,2R)-1-(hydroxymethyl)-2methylbutylamine was prepared from N-(tert-butoxycarbamoyl)-(L)-allo-isoleucine as described in Method B1a, Step 2. The carbamate was converted to (1S,2R)-1-(chloromethyl)-2-methylbutanammonium chloride as described in Method B7b. 2-Methyl-4-nitrophenyl isothiocyanate was reacted with (1S,2R)-1-(chloromethyl)-2-methylbutanammonium chloride to Method C1e to give (4S)-2-(2-methyl-4-nitrophenylimino)-4-((2R)-2-butyl)-1,3-thiazolidine. The thiazolidine was reacted with isobutyl bromide according to Method D2a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-4-((2R)-2-butyl)-3-isobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record
ord-66e05ea12541426cb038805546969a36
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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