Hydrochloric Acid → N-((3aS,4R,6aR)-2-((R)-2-amino-4-methylpentanoyl)octahydrocyclopenta[c]pyrrol-4-yl)-2,2-dicyclohexylacetamide

HRID 2363540Notes

Reaction equation

HRID 2363540 reaction equation
[CH:1]1([CH:7]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:8]([NH:10][C@H:11]2[C@H:18]3[C@H:14]([CH2:15][N:16]([C:19](=[O:33])[C@H:20]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:17]3)[CH2:13][CH2:12]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CCOCC>[NH2:25][C@H:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:19]([N:16]1[CH2:17][C@H:18]2[C@H:11]([NH:10][C:8](=[O:9])[CH:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:12][CH2:13][C@H:14]2[CH2:15]1)=[O:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131729483tert-butyl(R)-1-((3aS,4R,6aR)-4-(2,2-dicyclohexylacetamido)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1-oxopentan-2-ylcarbamate

Product 1

HCID 66590431N-((3aS,4R,6aR)-2-((R)-2-amino-4-methylpentanoyl)octahydrocyclopenta[c]pyrrol-4-yl)-2,2-dicyclohexylacetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

tert-Butyl(R)-1-((3aS,4R,6aR)-4-(2,2-dicyclohexylacetamido)hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-4-methyl-1-oxopentan-2-ylcarbamate (185 mg, 0.339 mmol) from Step A, and 2 N HCl in ether (2.5 mL, 5.00 mmol) were combined in ether (1 mL). The reaction mixture was stirred at room temperature overnight. The solids were collected and dried to give N-((3aS,4R,6aR)-2-((R)-2-amino-4-methylpentanoyl)octahydrocyclopenta[c]pyrrol-4-yl)-2,2-dicyclohexylacetamide: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.34-8.24 (m, 1H), 4.92 (br s, 2H), 4.46-4.31 (m, 1H), 4.07 (d, J=9.2, 0.5H), 3.91-3.81 (m, 1.5H), 3.77 (dd, J=8.8, 12.1, 1H), 3.72-3.64 (m, 0.5H), 3.59-3.53 (m, 0.5H), 3.45 (dd, J=5.2, 12.2, 0.5H), 3.32 (d, J=6.5, 0.5H), 2.82-2.69 (m, 1H), 2.63 (dd, J=8.4, 14.5, 0.5H), 2.54 (dd, J=8.0, 16.4, 0.5H), 2.21-2.06 (m, 2H), 2.02 (q, J=7.6, 1H), 1.99-1.55 (m, 15H), 1.50-1.38 (m, 3H), 1.37-1.12 (m, 9H), 1.09 (d, J=6.5, 3H), 1.01 (d, J=6.6, 2H), 0.96 (d, J=6.4, 1H), 0.91 (d, J=6.6, 1H). MS (ESI+) m/z 466 (M+H)+.

Workup

  1. customThe solids were collected
  2. customdried

Sources & evidence

ORD record
ord-6151225b07d4491dacf8ff6c169c538b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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