Sodium Bicarbonate → HCID 58485337, compound

HRID 1046251Notes

Reaction equation

HRID 1046251 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]([CH3:13])([OH:12])[CH3:11])=[N:6][CH:7]=1.[OH:14][C:15]([CH3:48])([CH3:47])[CH2:16][C@@:17]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:22][C:21](=[O:23])[N:20]([C@H:24]([C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH3:25])[CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:12][C:10]([CH3:13])([CH3:11])[CH2:9][O:8][C:5]1[N:6]=[CH:7][C:2]([C:29]2[CH:28]=[CH:27][C:26]([C@@H:24]([N:20]3[CH2:19][CH2:18][C@:17]([CH2:16][C:15]([OH:14])([CH3:47])[CH3:48])([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[O:22][C:21]3=[O:23])[CH3:25])=[CH:31][CH:30]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 57540519HCID 57540519, compoundHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 58485337HCID 58485337, compoundYield 12.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-(5-bromopyridin-2-yloxy)-2-methylpropan-2-ol (30 mg, 0.122 mmol) in DME (6 mL) was added Pd(PPh3)4 (10 mg) under nitrogen. The mixture was stirred for 1 h at rt. A solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one (58.4 mg, 0.122 mmol) in EtOH (2 mL) and satd aq NaHCO3 (2 mL) were added. The mixture was stirred at 100° C. for 2 h, quenched with water, and extracted with EtOAc (3×10 mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated, and purified by preparative TLC (1:1 PE/EtOAc) and HPLC to afford the title compound (7.6 mg, 12.1%). 1H NMR (CDCl3): δ 8.23 (d, 1H), 7.72 (q, 1H), 7.74-6.68 (m, 10H), 5.70 (m, 1H), 4.24 (s, 2H), 3.43 (s, 1H), 2.85 (m, 1H), 2.40 (m, 1H), 2.27-2.14 (m, 5H), 1.54 (d, 3H), 1.33-1.29 (d, 3H), 1.18-1.12 (d, 3H).

Workup

  1. additionwere added
  2. stirringThe mixture was stirred at 100° C. for 2 h
  3. customquenched with water
  4. extractionextracted with EtOAc (3×10 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. custompurified by preparative TLC (1:1 PE/EtOAc) and HPLC

Sources & evidence

ORD record
ord-2759a4f120544fbfb99dc1624b84a650
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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