(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride → (R)-4-[(S)-3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-methoxycarbonyl-propyl]-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

HRID 655569Notes

Reaction equation

HRID 655569 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([C@H:19]([C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH:21]=O)[CH2:13][C@H:12]1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:29]1[C:31]2([CH2:36][CH2:35][NH:34][CH2:33][C@H:32]2[OH:37])[CH2:30]1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]([C@H:19]([C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH2:21][N:34]2[CH2:35][CH2:36][C:31]3([CH2:30][CH2:29]3)[C@H:32]([OH:37])[CH2:33]2)[CH2:13][C@H:12]1[CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2×HCID 86638116(R)-4-((S)-1-methoxycarbonyl-3-oxo-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

Product 1

HCID 67080614(R)-4-[(S)-3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-methoxycarbonyl-propyl]-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl esterYield 42%

Procedure

In analogy to the procedure described for example 58D, (R)-4-((S)-1-methoxycarbonyl-3-oxo-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester and (S)-6-aza-spiro[2.5]octan-4-ol hydrochloride (intermediate 2) gave the title compound in 42% yield as yellow oil. MS: 488.4 (MH+).

Sources & evidence

ORD record
ord-ffef8919ec5b48b1b2bf14e2ea2c1f66
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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