Triethylamine → HCID 66706770, compound

HRID 2041424Notes

Reaction equation

HRID 2041424 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([S:20][CH2:21][CH2:22][OH:23])=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[CH3:31][C:32]([CH3:37])([CH3:36])[C:33](Cl)=[O:34]>C(Cl)Cl.O>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[S:20][CH2:21][CH2:22][O:23][C:33](=[O:34])[C:32]([CH3:37])([CH3:36])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 66706709HCID 66706709, compound

Product 1

HCID 66706770HCID 66706770, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-tert-butoxycarbonyl-7-chloro-6-(2-hydroxyethylthio)-2,3,4,5-tetrahydrobenzo[d]azepine (85 mg, 0.238 mmol) in DCM (3 ml) at 0° C., add triethylamine (331 2.381 mmol) followed by trimethylacetyl chloride (147 μl, 1.190 mmol). Continue stirring for 15 min, dilute with water, extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Deprotection by the General Procedure 1-5, basic workup, and by the General Procedure 2-2 give the title compound. MS (ES+) m/z 342 (M+H).

Workup

  1. extractionextract three times with EtOAc
  2. dry with materialdry over anhydrous Na2SO4
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-619326e38daa4247a7e22c7e65ad970a
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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