(5R,8S)-7-((S)-2-{(S)-2-Cyclohexyl-2-[((S)-1-isopropyl-piperidine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid methyl ester → (5R,8S)-7-((S)-2-{(S)-2-Cyclohexyl-2-[((S)-1-isopropyl-piperidine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid

HRID 1471320Notes

Reaction equation

HRID 1471320 reaction equation
C[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:45])[C@@H:18]([NH:23][C:24](=[O:44])[C@H:25]([CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[NH:26][C:27]([C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][N:30]1[CH:35]([CH3:37])[CH3:36])=[O:28])[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:4]>C1COCC1.CO.O>[CH:38]1([C@H:25]([NH:26][C:27]([C@@H:29]2[CH2:34][CH2:33][CH2:32][CH2:31][N:30]2[CH:35]([CH3:37])[CH3:36])=[O:28])[C:24]([NH:23][C@@H:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:17]([N:6]2[C@H:5]([C:3]([OH:4])=[O:2])[CH2:16][C@:8]3([C:13]([CH3:14])([CH3:15])[C:9]43[CH2:12][CH2:11][CH2:10]4)[CH2:7]2)=[O:45])=[O:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Participants

3

Reactant 1

HCID 59533292(5R,8S)-7-((S)-2-{(S)-2-Cyclohexyl-2-[((S)-1-isopropyl-piperidine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid methyl ester

Product 1

HCID 59533288(5R,8S)-7-((S)-2-{(S)-2-Cyclohexyl-2-[((S)-1-isopropyl-piperidine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of (5R,8S)-7-((S)-2-{(S)-2-Cyclohexyl-2-[((S)-1-isopropyl-piperidine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid methyl ester (0.69 g; 1.10 mmol) in THF/Methanol/water (2:1:1; 20 mL) was added LiOH monohydrate (0.138 g; 3.3 mmol) and the reaction was stirred overnight at room temperature. The solvent was removed in vacuo, water was added, the product was frozen in liquid nitrogen and lyophilized overnight to yield the title compound. LC-MS (method E): Rt=1.50 min; M/z=615 [M+]; HPLC (method A3): Rt=4.38 min

Workup

  1. customThe solvent was removed in vacuo, water
  2. additionwas added
  3. temperaturethe product was frozen in liquid nitrogen
  4. waitlyophilized overnight

Sources & evidence

ORD record
ord-cf82e8aeed7d42dc921ced13c5ce9854
Source dataset
uspto-grants-2015_04
Patent number
US09011833B2

Reaction notes

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