Diisopropylethylamine → HCID 178446312, compound

HRID 425132Notes

Reaction equation

HRID 425132 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH2:10])[CH2:7][N:6]1[C:11](=[O:36])[N:12]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[NH:30][N:29]=[N:28][N:27]=2)=[CH:16][CH:15]=1)=[O:4].[CH3:37][C:38]([CH3:54])([CH3:53])[C:39]([O:41][NH:42][C:43]([CH:45]([CH2:49][CH:50]([CH3:52])[CH3:51])[C:46](O)=[O:47])=[O:44])=[O:40].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:46](=[O:47])[CH:45]([C:43](=[O:44])[NH:42][O:41][C:39](=[O:40])[C:38]([CH3:53])([CH3:37])[CH3:54])[CH2:49][CH:50]([CH3:52])[CH3:51])[CH2:7][N:6]1[C:11](=[O:36])[N:12]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[NH:30][N:29]=[N:28][N:27]=2)=[CH:16][CH:15]=1)=[O:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594288372-(2,2-Dimethylpropionyloxycarbamoyl)-4-methylpentanoic acidHCID 178446310HCID 178446310, compound

Product 1

HCID 178446312HCID 178446312, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,4S)-4-Amino-1-{pentyl-[2′-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]carbamoyl}-pyrrolidine-2-carboxylic acid methyl ester (2.0 g, 3.0 mmol) and 2-(2,2-dimethyl-propionyloxycarbamoyl)-4-methylpentanoic acid (1.2 g, 1.4 equiv) were dissolved in DMF (20 mL). DIPEA (2 mL, 3.5 equiv) was added, followed by HATU (1.4 g, 1.2 equiv). The mixture was stirred for 16 hours at room temperature and then partitioned between water (100 mL) and EtOAc (100 mL). The layers were separated and the aqueous phase was re-extracted with EtOAc (100 mL). The combined organics were washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, and evaporated to afford the title compound (2.2 g, 3 mmol), which was used without further purification. MS m/z: [M+H]+ calcd for C38H52N8O7, 732.9. found 733.5.

Workup

  1. custompartitioned between water (100 mL) and EtOAc (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was re-extracted with EtOAc (100 mL)
  4. washThe combined organics were washed with saturated aqueous NaCl (100 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-d743568efe5745d49713acbcf6cd08da
Source dataset
uspto-grants-2012_01
Patent number
US08106082B2

Reaction notes

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