Hydrochloric Acid → (5R,8S)-7-[(S)-2-((S)-2-Amino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid methyl ester

HRID 1502203Notes

Reaction equation

HRID 1502203 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:16][C@:8]2([C:13]([CH3:15])([CH3:14])[C:9]32[CH2:12][CH2:11][CH2:10]3)[CH2:7][N:6]1[C:17](=[O:41])[C@@H:18]([NH:23][C:24](=[O:40])[C@@H:25]([NH:32]C(OC(C)(C)C)=O)[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:4].Cl>O1CCOCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:16][C@:8]2([C:13]([CH3:14])([CH3:15])[C:9]32[CH2:12][CH2:11][CH2:10]3)[CH2:7][N:6]1[C:17](=[O:41])[C@@H:18]([NH:23][C:24](=[O:40])[C@@H:25]([NH2:32])[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59533208HCID 59533208, compound

Product 1

HCID 59533249(5R,8S)-7-[(S)-2-((S)-2-Amino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (5R,8S)-7-[(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3,3-dimethyl-butyryl]-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid methyl ester (0.755 g; 1.31 mmol) and 4.9 mL HCl (4 M in dioxane) in 10 mL dioxane was stirred overnight at ambient temperature. The mixture was concentrated under reduced pressure to yield the title compound which was used in the next step without further purification. LC-MS (method E): Rt=1.47 min; M/z=476 [M+]; HPLC (method A3): Rt=4.27 min

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1964b728f5d14a048750ee5bb53b2b70
Source dataset
uspto-grants-2015_12
Patent number
US09206232B2

Reaction notes

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