Triethylamine → HCID 58313110, compound

HRID 1748864Notes

Reaction equation

HRID 1748864 reaction equation
[F:1][C:2]1([F:26])[CH2:25][CH2:24][C:5]2([CH2:9][N:8]([C:10](=[O:20])[C@H:11]([CH:17]([CH3:19])[CH3:18])[NH:12][C:13]([O:15][CH3:16])=[O:14])[C@H:7]([C:21]([OH:23])=[O:22])[CH2:6]2)[CH2:4][CH2:3]1.[CH3:27][O:28][C:29]([NH:31][C@H:32]([C:36]([N:38]1[CH2:64][CH2:63][CH2:62][C@H:39]1[C:40]([O:42][CH2:43][C:44]([C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55]([C:58](=[O:61])[CH2:59]Br)=[CH:54][CH:53]=2)=[CH:48][CH:47]=1)=[O:45])=[O:41])=[O:37])[CH:33]([CH3:35])[CH3:34])=[O:30].C(N(CC)CC)C>C(#N)C>[F:26][C:2]1([F:1])[CH2:25][CH2:24][C:5]2([CH2:9][N:8]([C:10](=[O:20])[C@@H:11]([NH:12][C:13]([O:15][CH3:16])=[O:14])[CH:17]([CH3:19])[CH3:18])[C@H:7]([C:21]([O:23][CH2:59][C:58]([C:55]3[CH:56]=[CH:57][C:52]([C:49]4[CH:48]=[CH:47][C:46]([C:44](=[O:45])[CH2:43][O:42][C:40]([C@@H:39]5[CH2:62][CH2:63][CH2:64][N:38]5[C:36](=[O:37])[C@@H:32]([NH:31][C:29]([O:28][CH3:27])=[O:30])[CH:33]([CH3:35])[CH3:34])=[O:41])=[CH:51][CH:50]=4)=[CH:53][CH:54]=3)=[O:61])=[O:22])[CH2:6]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58313132HCID 58313132, compoundHCID 58313148HCID 58313148, compound

Product 1

HCID 58313110HCID 58313110, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S)-8,8-difluoro-2-{N-[(methyloxy)carbonyl]-L-valyl}-2-azaspiro[4.5]decane-3-carboxylic acid (116) (168 mg, 0.45 mmol) and 2-[4′-(bromoacetyl)-4-biphenylyl]-2-oxoethyl N-[(methyloxy)carbonyl]-L-valyl-L-prolinate (70) (250 mg, 0.43 mmol) in anhydrous acetonitrile (2 mL) was added triethylamine (0.09 mL, 0.64 mmol) and the reaction stirred at room temperature under nitrogen for 1 h. The reaction was partitioned between EtOAc and 0.1 N HCl (30 mL each), the organic layer was washed with brine and dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 65-100% hexanes/EtOAc to afford the title compound as an off white solid (309 mg, 82% yield).

Workup

  1. customThe reaction was partitioned between EtOAc and 0.1 N HCl (30 mL each)
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 65-100% hexanes/EtOAc

Sources & evidence

ORD record
ord-c68f0f6f6d6a4fdaa7b74438fe2dfc09
Source dataset
uspto-grants-2015_10
Patent number
US09150587B2

Reaction notes

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