Dimethylformamide → HCID 67023487, compound

HRID 491886Notes

Reaction equation

HRID 491886 reaction equation
C([O:5][C:6]([NH:8][C@H:9](C1CCCCC1)[CH2:10][CH2:11]C(O)=O)=[O:7])(C)(C)C.[CH2:21]([N:28]1[C:32]([CH2:33][NH:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[N:31][N:30]=[N:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=N[C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][C:59]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN([CH:77]=[O:78])C>C(OCC)C>[CH2:21]([N:28]1[C:32]([CH2:33][N:34]([CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:77]([CH:59]2[CH2:60][CH2:61][CH2:62][C@@H:63]([CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:5])[OH:7])[CH2:64]2)=[O:78])=[N:31][N:30]=[N:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17756583HCID 17756583, compoundHCID 67023499HCID 67023499, compound

Product 1

HCID 67023487HCID 67023487, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 4-tert-butoxycarbonylamino-4-(S)-cyclohexyl-butyric acid (2.63 g, 9.2 mmole) were added (1-benzyl-1H-tetrazol-5-ylmethyl)-cyclohexyl-amine (2.50 g, 9.2 mmole) and N,N-diisopropylethylamine (3.2 mL, 18.4 mmole) in DMF (50 mL) and HBTU (4.19 g, 11.0 mmole). After stirring at room temperature overnight, the reaction mixture was diluted with diethyl ether (200 mL). The reaction mixture was extracted with water three times and dried over magnesium sulfate. The solution was concentrated to yield {3-[(1-benzyl-1H-tetrazol-5-ylmethyl)-cyclohexyl-carbamoyl]-(S)-cyclohexyl-propyl}-carbamic acid as a colorless oil.

Workup

  1. extractionThe reaction mixture was extracted with water three times
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-4a46719d6f0e4542a2e6f387a8a922ad
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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