Hydrochloric Acid → HCID 51348672, compound

HRID 1968863Notes

Reaction equation

HRID 1968863 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]([O:38][CH:39]([CH3:41])[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:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH:39]([CH3:40])[CH3:41])=[CH:36][CH:37]=2)=[CH:28][CH:27]=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 67438147HCID 67438147, compound

Product 1

HCID 51348672HCID 51348672, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ((1S,2S)-1-{[(4′-isopropoxy-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′-isopropoxy-biphenyl-4-yl)-amide (38 mg, 95% yield) as a white solid: 1H NMR (400 MHz, MeOD) δ 8.34 (d, J=5.3 Hz, 1H), 7.95 (t, J=7.6 Hz, 1H), 7.55 (d, J=8.1 Hz, 2H), 7.38-7.45 (m, 3H), 7.29-7.37 (m, 3H), 6.88 (d, J=8.6 Hz, 2H), 4.54 (dt, J=12.1, 6.1 Hz, 1H), 4.22 (dd, J=15.0, 9.0 Hz, 1H), 3.65 (dd, J=15.0, 2.7 Hz, 1H), 3.23-3.30 (m, 1H), 2.66-2.76 (m, 1H), 1.99-2.06 (m, 1H), 1.72-1.80 (m, 1H), 1.63-1.71 (m, 1H), 1.45-1.54 (m, 1H), 1.26-1.36 (m, 1H), 1.24 (d, J=6.1 Hz, 6H), 1.05-1.17 (m, 1H), 0.88 (d, J=6.8 Hz, 3H), 0.75 (t, 3H); LRMS (ESI) m/e 472.3 [(M+H)+, calcd for C30H38N3O2 472.3].

Workup

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

Sources & evidence

ORD record
ord-d2823190b43747cbacd939a4598a508f
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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