Methanesulfonamide → HCID 89545437, compound

HRID 709513Notes

Reaction equation

HRID 709513 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18](/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:17]3)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:55]C)C=C4)N(CC2)C1.CS(N)(=O)=O.CC(O)C.[OH2:101]>>[OH:101][C@H:26]([C@@H:25]([OH:55])[C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:32])[F:33])=[CH:8][N:7]=3)=[CH:11][CH:12]=2)[CH:17]=1)[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 21889133Propan-2-ol--water (1/1)HCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 117613621HCID 117613621, compound

Product 1

HCID 89545437HCID 89545437, compound

Procedure

(2R,3S)-Ethyl 2,3-dihydroxy-3-(1-(4-((5-(trifluoromethyl)pyridin-2-yl)oxy)-phenyl)-1H-indol-3-yl)propanoate (4) was prepared as follows: A mixture of compound 3 (0.12 g, 1.0 eq), Ad-Mix-α (1.5 eq, Aldrich), and MeSO2NH2 (Aldrich, 1.2 eq) in 10 mL of i-PrOH/water (1/1) was shaken at room temperature for 4 hours. The reaction was quenched with EtOAc/water (60 mL/20 mL). The organic layer was separated, washed with brine, concentrated and purified by column (EtOAc/hexanes 5/4) to give compound 4 as a colorless oil (80 mg): 1H-NMR (400 MHz, CDCl3) δ: 8.42 (s, 1H), 8.05 (s, 1H), 7.89 (1H, dd, 2.6 & 8.7 Hz), 7.77-7.8 (m, 1H), 7.5-7.57 (m, 3H), 7.18-7.28 (m, 4H), 7.04 (d, 1H, 8.8 Hz), 6.9 (s, 1H), 6.28 (d, 1H, 1.5 Hz), 4.36 (q, 2H, 7.1 Hz), 1.37 (t, 3H, 7.2 Hz).

Workup

  1. custom(2R,3S)-Ethyl 2,3-dihydroxy-3-(1-(4-((5-(trifluoromethyl)pyridin-2-yl)oxy)-phenyl)-1H-indol-3-yl)propanoate (4) was prepared
  2. customThe reaction was quenched with EtOAc/water (60 mL/20 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. concentrationconcentrated
  6. custompurified by column (EtOAc/hexanes 5/4)

Sources & evidence

ORD record
ord-8d66a00555c84b91b6960094de569553
Source dataset
uspto-grants-2015_11
Patent number
US09181185B2

Reaction notes

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