tert-Butoxycarbonyl-L-isoleucine → HCID 58434130, compound

HRID 1188253Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C@@H:12]([NH2:17])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:18]([NH:25][C@H:26]([C:31](O)=[O:32])[C@H:27]([CH2:29][CH3:30])[CH3:28])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>>[C:18]([NH:25][C@@H:26]([C@@H:27]([CH3:28])[CH2:29][CH3:30])[C:31]([NH:17][C@H:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:32])([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19]

Participants

Reactant 2

HCID 2724762tert-Butoxycarbonyl-L-isoleucine

HCID 9794968(-)-Didesmethylsibutramine

Product 1

HCID 58434130HCID 58434130, compound

Procedure

By similar method as example 2, resolved (S)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine (II-S) (250 mg) was condensed with Boc-L-isoleucine (210 mg) to give the title compound (2S,3S)-2-(Boc-amino)-N-{(S)-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}-3-methylvaleramide.

Sources & evidence

ORD record: ord-b4dba222d4d348d7bf6955c3d8d1ffe4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673981B2

Reaction notes

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