Hydrochloric Acid → HCID 71512289, compound

HRID 1914493Notes

Reaction equation

HRID 1914493 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C@@H:24]3[C@@H:28]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=4)[CH2:27][O:26][C:25]3=[O:40])=[CH:19][C:18]=2[O:41][CH3:42])=[O:15])[CH2:10]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C@@H:24]3[C@@H:28]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([O:38][CH3:39])[CH:31]=4)[CH2:27][O:26][C:25]3=[O:40])=[CH:19][C:18]=2[O:41][CH3:42])=[O:15])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86676735HCID 86676735, compound

Product 1

HCID 71512289HCID 71512289, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl 3-((tert-butoxycarbonyl)amino)pyrrolidine-1-carboxylate (96 mg, 0.16 mmol, 1.0 eq) was added a solution of HCl in dioxane. The resulting mixture was stirred at rt for 3 h, and then concentrated and washed with THF to afford (S)-4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl 3-aminopyrrolidine-1-carboxylate (27 mg, 36.4%). LRMS (M+H+) m/z calculated 485.2, found 484.9. 1H NMR (DMSO-d6, 400 MHz) δ 8.54 (brs, 3H), 6.98-7.01 (m, 1H), 6.93 (s, 1H), 6.83 (d, 1H), 6.77 (d, 1H), 6.66 (s, 1H), 6.60 (d, 1H), 4.10-4.14 (m, 1H), 3.81-3.93 (m, 3H), 3.73 (s, 3H), 3.70 (s, 6H), 3.54-3.64 (m, 2H), 3.39-3.52 (m, 3H), 2.76-2.92 (m, 3H), 2.47-2.50 (m, 1H), 2.01-2.28 (m, 2H).

Workup

  1. concentrationconcentrated
  2. washwashed with THF

Sources & evidence

ORD record
ord-2bb6aa8407624818ad24408fb0991523
Source dataset
uspto-grants-2013_12
Patent number
US08614211B2

Reaction notes

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