3,4-Dimethylphenyl isocyanate → (R)-4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid (3,4-dimethyl-phenyl)-amide

HRID 655571Notes

Reaction equation

HRID 655571 reaction equation
Cl.Cl.[OH:3][C@@H:4]1[CH2:11][N:10]([CH2:12][CH2:13][CH2:14][N:15]2[C:21](=[O:22])[CH2:20][CH2:19][NH:18][C@H:17]([CH3:23])[CH2:16]2)[CH2:9][CH2:8][C:5]21[CH2:7][CH2:6]2.[CH3:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31]>>[CH3:24][C:25]1[CH:26]=[C:27]([NH:32][C:33]([N:18]2[CH2:19][CH2:20][C:21](=[O:22])[N:15]([CH2:14][CH2:13][CH2:12][N:10]3[CH2:9][CH2:8][C:5]4([CH2:6][CH2:7]4)[C@H:4]([OH:3])[CH2:11]3)[CH2:16][C@H:17]2[CH3:23])=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31]

Participants

3

Reactant 2

HCID 43896633,4-Dimethylphenyl isocyanateHCID 67080697(R)-4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-[1,4]diazepan-5-one dihydrochloride

Product 1

HCID 59149950(R)-4-[3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid (3,4-dimethyl-phenyl)-amideYield 32%

Procedure

In analogy to the procedure described in example 58F, (R)-4-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-2-methyl-[1,4]diazepan-5-one dihydrochloride (example 58E) and 3,4-dimethylphenyl isocyanate (without addition of 0.1 eq. of 3,4-dimethylphenyl isocyanate) gave 0.035 g (32%) of the title compound as white foam. MS: 443.3 (MH+).

Sources & evidence

ORD record
ord-83a999dfc58f453da294e70d6b184b01
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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