Hydrochloric Acid → HCID 58466521, compound

HRID 1968864Notes

Reaction equation

HRID 1968864 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:13][N:14]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH3:40])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[C:15]([CH:17]1[CH2:19][CH:18]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=[O:16])[C@@H:9]([CH3:12])[CH2:10][CH3:11])(C)(C)C.ClCCl.Cl>O1CCOCC1>[NH2:7][C@@H:8]([C@@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:13][N:14]([C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH3:40])=[CH:34][CH:33]=2)=[CH:30][CH:31]=1)[C:15]([C@@H:17]1[CH2:19][C@H:18]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 67438870HCID 67438870, compound

Product 1

HCID 58466521HCID 58466521, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ((1S,2S)-1-{[(4′-propyl-biphenyl-4-yl)-(2-pyridin-2-yl-cyclopropanecarbonyl)-amino]-methyl}-2-methyl-butyl)-carbamic acid tert-butyl ester (48 mg, 0.084 mmol) and dichloromethane (4 mL) was treated with a solution of HCl in dioxane (4 N, 0.5 mL) and the resulting reaction mixture was maintained at room temperature for 12 h. The reaction was then concentrated to dryness to afford (1R,2R)-2-pyridin-2-yl-cyclopropanecarboxylic acid ((2S,3S)-2-amino-3-methyl-pentyl)-(4′-propyl-biphenyl-4-yl)-amide (38 mg, 95% yield) as a white solid: 1H NMR (400 MHz, MeOD) δ 8.31 (d, J=5.1 Hz, 1H), 7.86-7.95 (m, 1H), 7.57 (d, J=8.1 Hz, 2H), 7.33-7.43 (m, 5H), 7.30 (d, J=8.1 Hz, 1H), 7.17 (d, J=8.1 Hz, 2H), 4.21 (dd, J=14.9, 9.1 Hz, 1H), 3.65 (d, J=14.9 Hz, 1H), 3.23-3.29 (m, 1H), 2.64-2.73 (m, 1H), 2.53 (t, J=7.6 Hz, 2H), 1.96-2.05 (m, 1H), 1.70-1.78 (m, 1H), 1.61-1.70 (m, 1H), 1.57 (dd, J=15.2, 7.6 Hz, 2H), 1.43-1.51 (m, 1H), 1.22-1.36 (m, 1H), 1.05-1.17 (m, 1H), 0.82-0.90 (m, 6H), 0.75 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 456.3 [(M+H)+, calcd for C30H38N3O 456.3].

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction was then concentrated to dryness

Sources & evidence

ORD record
ord-1f05ac07d0784fbaa8c2af5cb4cbc4d4
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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