(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 1502205Notes

Reaction equation

HRID 1502205 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-8d08ff2db13141c1a2b238cc26412bd7
Source dataset
uspto-grants-2015_12
Patent number
US09206232B2

Reaction notes

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