Hydrochloric Acid → (1S,3S)-1-((1S)-1-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-2-phenylethyl)-3-({(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}amino)-4-(4-pyridin-2-ylphenyl)butyl (2S)-2-aminopropanoate

HRID 1174410Notes

Reaction equation

HRID 1174410 reaction equation
C(OC([NH:8][C@H:9]([C:11]([O:13][C@H:14]([C@@H:43]([NH:51][C:52](=[O:71])[C@@H:53]([N:58]1[CH2:62][CH2:61][N:60]([CH2:63][C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:59]1=[O:70])[C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:15][C@@H:16]([NH:30][C:31](=[O:42])[C@H:32]([C:38]([CH3:41])([CH3:40])[CH3:39])[NH:33][C:34]([O:36][CH3:37])=[O:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][CH:19]=1)=[O:12])[CH3:10])=O)(C)(C)C.Cl>ClCCl.O1CCOCC1>[NH2:8][C@@H:9]([CH3:10])[C:11]([O:13][C@H:14]([C@@H:43]([NH:51][C:52](=[O:71])[C@@H:53]([N:58]1[CH2:62][CH2:61][N:60]([CH2:63][C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)[C:59]1=[O:70])[C:54]([CH3:55])([CH3:57])[CH3:56])[CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:15][C@@H:16]([NH:30][C:31](=[O:42])[C@@H:32]([NH:33][C:34]([O:36][CH3:37])=[O:35])[C:38]([CH3:39])([CH3:40])[CH3:41])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:22][CH:23]=1)=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86599589(1S,3S)-1-((1S)-1-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-2-phenylethyl)-3-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-4-(4-pyridin-2-ylphenyl)butyl N-(tert-butoxycarbonyl)-L-alaninate

Product 1

HCID 67406424(1S,3S)-1-((1S)-1-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-2-phenylethyl)-3-({(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}amino)-4-(4-pyridin-2-ylphenyl)butyl (2S)-2-aminopropanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Example 193A (0.098 g, 0.037 mmol) in dichloromethane (1.0 mL) at room temperature was added a solution of HCl in dioxane (0.13 mL, 4 N), and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated to give the title compound as the bis hydrochloride salt (0.089 g). 1H NMR (300 MHz, DMSO-d6), δ ppm 0.88 (s, 9 H), 0.91 (s, 9 H), 1.57 (d, J=7.4 Hz, 1 H), 1.69-1.74 (m, 2 H), 2.27 (q, J=9.6 Hz, 1 H), 2.53-2.56 (m, 2 H), 2.72-2.85 (m, 3 H), 2.94 (q, J=8.8 Hz, 1 H), 3.17-3.24 (m, 1 H), 3.46 (s, 3 ), 3.87 (d, J=9.9 Hz, 1 H), 4.14 (s, 1 H), 4.19-4.37 (m, 4 H), 4.31 (s, 2 H), 4.60-4.70 (m, 1 H), 5.14 (t, J=7.4 Hz, 1 H), 6.66 (d, J=9.6 Hz, 1 H), 7.00-7.08 (m, 3 H), 7.08-7.16 (m, 2 H), 7.26-7.47 (m, 8 H), 7.90-7.99 (m, 6 H), 8.46-8.57 (m, 3 H), 8.67-8.68 (m, 1 H).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4148f9c45f944a7eb46d293f547e94da
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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