Diisopropylethylamine → HCID 86670838, compound

HRID 709364Notes

Reaction equation

HRID 709364 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:21]([CH3:23])[CH3:22])[C:7]([N:9]1[C@H:17]([C:18](O)=[O:19])[CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10]1)=[O:8])=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:49][CH2:50][C:51]([C:53]1[CH:58]=[CH:57][C:56]([Br:59])=[CH:55][CH:54]=1)=[O:52].CCN(C(C)C)C(C)C>[Cl-].[Na+].O.CN(C=O)C>[Br:59][C:56]1[CH:55]=[CH:54][C:53]([C:51](=[O:52])[CH2:50][NH:49][C:18]([C@@H:17]2[CH2:16][C:11]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:10][N:9]2[C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:21]([CH3:22])[CH3:23])=[O:19])=[CH:58][CH:57]=1

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58313066HCID 58313066, compound

Product 1

HCID 86670838HCID 86670838, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In a 50 mL flask, (S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonane-8-carboxylic acid (110 mg, 333 μmol) was combined with DMF (5.00 ml) to give a colorless solution. HATU (127 mg, 333 μmol) was added and stirred at room temperature for 10 min followed by addition of 2-amino-1-(4-bromophenyl)ethanone HCl (83.3 mg, 333 μmol, Eq: 1.00). DIPEA (129 mg, 174 μl, 999 μmol) was then added dropwise and the suspension became a yellow solution once the DIPEA was added. It was stirred at room temperature for 1 hr then poured into brine solution (80 ml). The precipitate was filtered and washed with H2O then dissolved in CH2Cl2 (50 ml), It was dried with MgSO4, filtered and concentrated in vacuo to afford methyl(S)-1-((S)-8-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamate as a yellow solid (75 mg, 42.8%). ESI-LRMS m/e calcd for C22H28BrN3O7 [M+] 526. found 527 [M+H+].

Workup

  1. customto give a colorless solution
  2. additionwas added
  3. stirringIt was stirred at room temperature for 1 hr
  4. filtrationThe precipitate was filtered
  5. washwashed with H2O
  6. dissolutionthen dissolved in CH2Cl2 (50 ml)
  7. dry with materialIt was dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfa66c9643484d26b08090daed3ddb89
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

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