2-oxo-2-phenylethyl (3R,4S)-3-azido-1-[N-(tert-butoxycarbonyl)-4-(trifluoromethyl)phenylalanyl]-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxylate → HCID 67517051, compound

HRID 590748Notes

Reaction equation

HRID 590748 reaction equation
[N:1]([C@:4]1([C:43]([O:45]CC(=O)C2C=CC=CC=2)=[O:44])[C@@H:8]([CH2:9][CH2:10][CH2:11][B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)[CH2:7][N:6]([C:21](=[O:42])[C@H:22]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:5]1)=[N+]=[N-]>C(O)(=O)C.[Zn]>[NH2:1][C@:4]1([C:43]([OH:45])=[O:44])[C@@H:8]([CH2:9][CH2:10][CH2:11][B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:19])([CH3:20])[O:13]2)[CH2:7][N:6]([C:21](=[O:42])[C@H:22]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:36][CH:37]=2)[NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:5]1

Participants

4

Reactant 1

HCID 866657932-oxo-2-phenylethyl (3R,4S)-3-azido-1-[N-(tert-butoxycarbonyl)-4-(trifluoromethyl)phenylalanyl]-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxylate

Product 1

HCID 67517051HCID 67517051, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred solution of 2-oxo-2-phenylethyl (3R,4S)-3-azido-1-[N-(tert-butoxycarbonyl)-4-(trifluoromethyl)phenylalanyl]-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxylate (Step 1) in acetic acid (9 mL) was treated with zinc (201 mg, 3.08 mmol, 10 equiv), and the heterogeneous mixture was stirred at room temperature. After 1.25 h, the reaction was filtered, the filter pad was washed with acetic acid and ethyl acetate, and the filtrate was concentrated and dried under reduced pressure to give the crude (3R,4S)-3-amino-1-[N-(tert-butoxycarbonyl)-4-(trifluoromethyl)phenylalanyl]-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidine-3-carboxylic acid (242 mg) as a clear film which was used without further purification. LC-MS ESI+ MS found for C29H43BF3N3O7 m/z 614.3 (M+H); ESI− MS m/z 612.3 (M−H).

Workup

  1. filtrationthe reaction was filtered
  2. washthe filter pad was washed with acetic acid and ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3aa20b9decd64b5d8ea36654f184c2aa
Source dataset
uspto-grants-2016_01
Patent number
US09233985B2

Reaction notes

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