Triethylamine → HCID 66706770, compound

HRID 911554Notes

Reaction equation

HRID 911554 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 μl, 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-d68b12e048354ada80173fb3ee23537e
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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