N-((tert-Butoxy)carbonyl)-D-tryptophan → (R)-2-(tert-butoxycarbonylamino)-3-(1-isopropyl-1H-indol-3-yl)propanoic Acid

HRID 2070137Notes

Reaction equation

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

Participants

Reactant 2

HCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophan

HCID 598985Isopropyl tosylate

Product 1

HCID 59620335(R)-2-(tert-butoxycarbonylamino)-3-(1-isopropyl-1H-indol-3-yl)propanoic AcidYield 43.3%

Procedure

The procedure of Referential Example 1(a) was repeated, except that N-tert-butoxycarbonyl-D-tryptophan (3.0 g) and isopropyl 4-methylbenzenesulfonate (3.17 g) were used, whereby the title compound (1.48 g) was yielded.

Sources & evidence

ORD record: ord-8b8e39185fb5486e86a5e79829c2fec2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299255B2

Reaction notes

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