L-Leucinol → 4-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-benzamide

HRID 1061306Notes

Reaction equation

HRID 1061306 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH2:20][C@H:21]([CH2:26][OH:27])[CH2:22][CH:23]([CH3:25])[CH3:24]>>[O:1]1[C:5]2([CH2:6][CH2:7][N:8]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:20][C@H:21]([CH2:26][OH:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:16])=[CH:18][CH:19]=3)[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 111307L-LeucinolHCID 159484254-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid

Product 1

HCID 696547704-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)-N-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-benzamide

Procedure

The title compound was prepared from 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-benzoic acid (which was obtained in Example 150) (0.53 g, 2 mmol) and (S)-leucinol (0.30 g, 2.5 mmol) according to the procedure shown for Example 154 to give 0.53 g of a white solid; m.p. 90-91° C.; MS (ES) m/z: 363.3 (MH+); HRMS (ES) Calcd. for C20H31N2O4 (MH+): 363.2278, Found: 363.2275.

Sources & evidence

ORD record
ord-5954ec8ea2c24874887154add3d2d907
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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