Hydrochloric Acid → Hydrochloric Acid

HRID 527745Notes

Reaction equation

HRID 527745 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:37]=[CH:36][C:8]([CH2:9][O:10][C@@H:11]2[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23](=[O:35])[NH:24][C@H:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH2:28][CH2:27][CH2:26]3)[CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[ClH:38]>C(Cl)Cl>[C@H:25]1([NH:24][C:23]([C@H:13]2[NH:14][CH2:15][C@@H:11]([O:10][CH2:9][C:8]3[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:37][CH:36]=3)[CH2:12]2)=[O:35])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1.[ClH:38]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89930896HCID 89930896, compound

Product 2

HCID 313Hydrochloric AcidYield 1,222.5%HCID 89922260HCID 89922260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-tert-butyl 4-((4-(methoxycarbonyl)benzyl)oxy)-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidine-1-carboxylate (1.31 g, 2.58 mmol) in DCM (10 mL) was added HCl (4.0 M solution in dioxane, 12.9 mL, 51.5 mmol). The reaction mixture was stirred at rt for 1.5 h and concentrated in vacuo to give the title compound as a HCl salt (1.15 g, 100%, white solid). 1H NMR (DMSO-d6) δ 8.83 (d, J=8.4 Hz, 1H), 8.74 (d, J=8.6 Hz, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.46 (d, J=8.4 Hz, 2H), 7.26-7.00 (m, 3H), 5.05-4.88 (m, 1H), 4.56 (q, J=12.8 Hz, 2H), 4.31 (br. s., 2H), 3.86 (s, 3H), 3.55-3.46 (m, 1.5H), 2.81-2.61 (m, 2.5H), 2.48-2.21 (m, 2H), 1.84-1.53 (m, 4H); MS(ESI+) m/z 409.4 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0a149b07424d40dfadca5cda2c41509f
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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