Hydrochloric Acid → HCID 178473398, compound

HRID 576545Notes

Reaction equation

HRID 576545 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:46])[C@@H:13]([NH:38]C(OC(C)(C)C)=O)[CH2:14][CH2:15][CH2:16][NH:17]/[C:18](/[NH2:37])=[N:19]/[S:20]([C:23]2[C:24]([CH3:36])=[C:25]([CH3:35])[C:26]3[O:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]=3[C:33]=2[CH3:34])(=[O:22])=[O:21])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.O1CCOCC1>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12](=[O:46])[C@@H:13]([NH2:38])[CH2:14][CH2:15][CH2:16][NH:17]/[C:18](/[NH2:37])=[N:19]/[S:20]([C:23]2[C:24]([CH3:36])=[C:25]([CH3:35])[C:26]3[O:30][C:29]([CH3:31])([CH3:32])[CH2:28][C:27]=3[C:33]=2[CH3:34])(=[O:22])=[O:21])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178473382HCID 178473382, compound

Product 1

HCID 178473398HCID 178473398, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound F (20.2 g, 30.2 mmol) in dichloromethane (90 mL) was treated with 4.0 N HCl in 1,4-dioxane (90 mL, 363.3 mmol) and stirred at room temperature for 2 h. Next most of the dichloromethane was removed in vacuo and Et2O (˜1 L) was added. The resultant precipitate was filtered off and washed with Et2O and dried in vacuo to afford compound G (17.8 g, 30.2 mmol). LC-MS [M+H] 567.8 (C26H42N6O6S+H, calc: 567.8).

Workup

  1. customNext most of the dichloromethane was removed in vacuo and Et2O (˜1 L)
  2. additionwas added
  3. filtrationThe resultant precipitate was filtered off
  4. washwashed with Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0f50a4084f36488da52fe32c182be90a
Source dataset
uspto-grants-2015_05
Patent number
US09040032B2

Reaction notes

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