Hydrochloric Acid → 903579-36-2

HRID 605572Notes

Reaction equation

HRID 605572 reaction equation
C(OC([N:8]1[CH2:15][C@H:14]2[N:16](C(OC(C)(C)C)=O)[C@H:10]([CH2:11][C:12]([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][O:48][C:49]4[C:54]([Cl:55])=[CH:53][C:52]([CH3:56])=[CH:51][C:50]=4[Cl:57])=[CH:41][CH:40]=3)=[C:13]2[C:24](=[O:38])[N:25]([CH:35]2[CH2:37][CH2:36]2)[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:28]=2[CH3:34])[CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl>[CH:35]1([N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:28]=2[CH3:34])[C:24]([C:13]2[C@@H:14]3[NH:16][C@H:10]([CH2:11][C:12]=2[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][O:48][C:49]4[C:54]([Cl:55])=[CH:53][C:52]([CH3:56])=[CH:51][C:50]=4[Cl:57])=[CH:41][CH:40]=2)[CH2:9][NH:8][CH2:15]3)=[O:38])[CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86621185HCID 86621185, compound

Product 1

HCID 11578126903579-36-2Yield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A sol. of compound 10 (13.8 g, 16.9 mmol) in CH2Cl2 (120 mL) was cooled to 0° C. HCl (4M in dioxane, 120 mL) was added. The mixture was stirred for 1 h at 0° C., then 2 h at rt. The solvents were removed under reduced pressure, and the residue was dried under high vacuum. The residue was diluted with CH2Cl2, and washed with aq. 1M NaOH until the aq. layer staid basic. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (MeOH/CH2Cl2 5:95→10:90→20:80 with 1% Et3N all the time) yielded the title compound (9.45 g, 90%). LC-MS: tR=0.87 min; ES+: 620.40.

Workup

  1. custom2 h
  2. customat rt
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was dried under high vacuum
  5. additionThe residue was diluted with CH2Cl2
  6. washwashed with aq. 1M NaOH until the aq. layer staid basic
  7. dry with materialextracts were dried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the residue by FC (MeOH/CH2Cl2 5:95→10:90→20:80 with 1% Et3N all the time)

Sources & evidence

ORD record
ord-42cf549915cb4e73b633530918ae5d4a
Source dataset
uspto-grants-2011_03
Patent number
US07915259B2

Reaction notes

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