Hydrochloric Acid → HCID 51348956, compound

HRID 1968862Notes

Reaction equation

HRID 1968862 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][O: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:31]=[CH:30][C:29]([C:32]2[CH:33]=[CH:34][C:35]([CH2:38][O:39][CH3:40])=[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 67437238HCID 67437238, compound

Product 1

HCID 51348956HCID 51348956, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of ((1S,2S)-1-{[(4′-methoxymethyl-biphenyl-4-yl)-(2-pyridin-2-yl-cyclopropanecarbonyl)-amino]-methyl}-2-methyl-butyl)-carbamic acid tert-butyl ester (25 mg, 0.045 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′-methoxymethyl-biphenyl-4-yl)-amide (18 mg, 95% yield) as a white solid: 1H NMR (400 MHz, MeOD) δ 8.49 (d, J=5.8 Hz, 1H), 8.23 (t, J=7.8 Hz, 1H), 7.61-7.71 (m, 3H), 7.44-7.54 (m, 5H), 7.34 (d, J=8.1 Hz, 2H), 4.40 (s, 2H), 4.22 (dd, J=14.9, 9.1 Hz, 1H), 3.70 (dd, J=14.9, 2.5 Hz, 1H), 3.62-3.66 (m, 1H), 3.54-3.59 (m, 1H), 3.46-3.50 (m, 1H), 3.31 (s, 3H), 2.83-2.90 (m, 1H), 2.07-2.13 (m, 1H), 1.84-1.92 (m, 1H), 1.64-1.74 (m, 1H), 1.60 (dt, J=8.7, 5.5 Hz, 1H), 1.24-1.36 (m, 1H), 1.06-1.22 (m, 1H), 0.88 (d, J=6.8 Hz, 3H), 0.76 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 458.1 [(M+H)+, calcd for C29H36N3O2 458.3].

Workup

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

Sources & evidence

ORD record
ord-0defece43a7545daa9f919f7c09ddae1
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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