L-Tartaric acid → 1-(5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenyl)-3-((1S,2R)-4-fluoro-1-hydroxy-2,3-dihydro-1H-indene-2-yl)urea

HRID 243800Notes

Reaction equation

HRID 243800 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][C@@H:25]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][C:31]=2[F:34])[C@@H:26]1[OH:35].C(O)(=O)[C@@H]([C@H](C(O)=O)O)O>>[C:1]([C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]([O:20][CH3:21])=[C:9]([NH:11][C:12]([NH:24][C@@H:25]2[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[F:34])[C@@H:26]2[OH:35])=[O:19])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 444305L-Tartaric acidHCID 51441302(1S,2R)-2-amino-4-fluoro-2,3-dihydro-1H-indene-1-olHCID 681068792,2,2-Trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate

Product 1

HCID 681073101-(5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenyl)-3-((1S,2R)-4-fluoro-1-hydroxy-2,3-dihydro-1H-indene-2-yl)ureaYield 32%

Procedure

Using 2,2,2-trichloroethyl 5-tert-butyl-3-(hydroxymethyl)-2-methoxyphenylcarbamate (0.100 g, 0.260 mmol) and (1S,2R)-2-amino-4-fluoro-2,3-dihydro-1H-indene-1-ol.L-tartaric acid salt (0.091 g, 0.286 mmol), the same reaction as in Example 1 (5th Step) was carried out to obtain 0.034 g of the captioned compound (32% yield).

Sources & evidence

ORD record
ord-27528cbbc8bc42c59708282e82873cc4
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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