Dichloromethane methanol → Hydrochloric Acid

HRID 2095494Notes

Reaction equation

HRID 2095494 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)[C:13](=[O:24])[C@@H:12]1[CH3:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]1[C:28]2([CH2:33][CH2:32][NH:31][CH2:30][C@H:29]2[OH:34])[CH2:27]1.[Cl:35]CCl.CO>>[ClH:35].[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([N:31]2[CH2:32][CH2:33][C:28]3([CH2:26][CH2:27]3)[C@H:29]([OH:34])[CH2:30]2)=[O:23])[C:13](=[O:24])[C@@H:12]1[CH3:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 21226129Dichloromethane methanolHCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 67074539(S)-4-(4-carboxy-butyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Product 2

HCID 313Hydrochloric AcidHCID 67074445(S)-4-[5-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

Procedure

In analogy to the procedure described in Example 15, (S)-4-(4-carboxy-butyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester and 1.1 eq. of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave after flash chromatography (SiO2, dichloromethane/MeOH 100% dichloromethane to 85/15) the titled compound in 61% yield as light yellow amorphous solid. MS: 458.26 (MH+).

Sources & evidence

ORD record
ord-cb454445c40c494883b83ffd40e66edc
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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