Dichloromethane → ((S)-2-Azepan-1-yl-1-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-2-oxoethyl)-carbamic acid tert-butyl ester

HRID 389648Notes

Reaction equation

HRID 389648 reaction equation
C(C1C(N2CCOCC2=O)=CC=CC=1S([NH:19][C@H:20]([C:31]([N:33]1[CH2:38][CH2:37]OC[C@@H:34]1[CH3:39])=[O:32])[CH2:21][NH:22][C:23]([C:25]1[S:26][C:27]([Cl:30])=[CH:28][CH:29]=1)=[O:24])(=O)=O)C.N1[CH2:46][CH2:45][CH2:44]CCC1.[B-](F)(F)(F)F.CC[O:54][C:55](C(C#N)=NOC(N(C)C)=[N+](C)C)=[O:56].[CH3:69][CH2:70]N(C(C)C)C(C)C.[CH2:78](Cl)Cl>>[C:45]([O:56][C:55](=[O:54])[NH:19][C@@H:20]([CH2:21][NH:22][C:23]([C:25]1[S:26][C:27]([Cl:30])=[CH:28][CH:29]=1)=[O:24])[C:31]([N:33]1[CH2:34][CH2:39][CH2:70][CH2:69][CH2:37][CH2:38]1)=[O:32])([CH3:44])([CH3:46])[CH3:78]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8119AzepaneHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 44200855HCID 44200855, compound

Product 1

HCID 67155359((S)-2-Azepan-1-yl-1-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-2-oxoethyl)-carbamic acid tert-butyl ester

Procedure

To stirred intermediate 1 (1.5 g, 4.3 mmol) in 20 ml DCM was added azepane (426 mg, 4.3 mmol), TOTU (1.692 g, 5.16 mmol) and DIPEA (1.46 ml, 8.60 mmol). After 2 h the mixture was washed subsequently with sat. aq NaHCO3, and brine. The organic layer was dried with MgSO4, filtered and evaporated. The crude material (2.2 g) was used without further purification in the next step.

Workup

  1. washAfter 2 h the mixture was washed subsequently with sat. aq NaHCO3, and brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material (2.2 g) was used without further purification in the next step

Sources & evidence

ORD record
ord-a94ff4e10ded4d37a2f6c6b2fe70e83e
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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