Hydrochloric Acid → HCID 86701310, compound

HRID 2283008Notes

Reaction equation

HRID 2283008 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]([CH3:26])[O:15][C:14](=[O:27])[C@H:13]([NH:28]C(=O)OC(C)(C)C)[CH2:12][O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:36].O1CCOCC1>C(Cl)Cl>[ClH:36].[NH2:28][C@@H:13]1[CH2:12][O:11][CH2:10][C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]([CH3:26])[O:15][C:14]1=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86701312HCID 86701312, compound

Product 1

HCID 86701310HCID 86701310, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((3R,7S,8S,9R)-7,8-bis(benzyloxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)carbamate (104.0 mg, 0.214 mmol) in DCM (1.20 mL) was added a 4.0 M solution of HCl in dioxane (1.07 mL, 4.28 mmol) and the reaction was stirred at room temperature for 2 h. The solvent was removed under vacuum and the residue was dried under high vacuum to yield the title compound as an off-white oil (85.0 mg, 94%): IR (neat) 3365, 1636, 1235, 1063 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.76 (bs, 2H), 7.35-7.20 (m, 10H), 5.30 (s, 1H), 4.69-4.45 (m, 5H), 4.20 (d, J=9.1 Hz, 2H), 3.89-3.75 (m, 2H), 3.59 (d, J=11.1 Hz, 1H), 3.47 (d, J=7.1 Hz, 1H), 1.32 (d, J=6.8 Hz, 3H); HRMS-ESI (m/z) [M]+ calcd for C22H27NO5, 385.1889; found, 385.1890.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-cfae25efc3824b7ebf6bda413de17c7b
Source dataset
uspto-grants-2015_09
Patent number
US09144239B2

Reaction notes

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