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Cesium carbonate → (2S,3R,6S)-4-[4-(4-hydroxy-4-methyl-pent-2-ynyloxy)-benzenesulfonyl]-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

HRID 1935342
Notes
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Reaction equation

HRID 1935342 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([CH3:11])[O:9][C@@H:8]([CH3:12])[CH2:7][N:6]1[S:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14])=[O:4].I[CH2:24][C:25]#[C:26][C:27]([CH3:30])([OH:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)C>[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([CH3:11])[O:9][C@@H:8]([CH3:12])[CH2:7][N:6]1[S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:24][C:25]#[C:26][C:27]([OH:29])([CH3:30])[CH3:28])=[CH:20][CH:21]=1)(=[O:15])=[O:14])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 120166895-Iodo-2-methyl-pent-3-yn-2-olHCID 12016690(2S,3R,6S)-4-(4-Hydroxy-benzenesulfonyl)-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

Product 1

HCID 12016682(2S,3R,6S)-4-[4-(4-hydroxy-4-methyl-pent-2-ynyloxy)-benzenesulfonyl]-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

(2S,3R,6S)-4-(4-Hydroxy-benzenesulfonyl)-2,6-dimethyl-morpholine-3-carboxylic acid methyl ester, (200 mg, 0.607 mmol) (prepared according to the methods described in U.S. patent application Ser. No. 60/096256, filed Aug. 12, 1998) was dissolved in dimethyl formamide (6 mL). 5-Iodo-2-methyl-pent-3-yn-2-ol (272 mg, 1.214 mmol) and cesium carbonate (593 mg, 1.821 mmol) were added and the reaction stirred at room temperature for 4 hours. The reaction was diluted with diethyl ether (100 mL) and washed with water (5 times 10 mL) and brine (30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound. The crude material was used directly in the preparation of Example 1 without further purification. 1HNMR (400 MHz, CDCl3): δ=7.70 (d, J=8.9 Hz, 2H), 7.0 (d, J=8.9 Hz, 2H), 4.74 (bs, 2H), 4.50 (q, J=6.6 Hz, 1H), 4.26 (s, 1H), 3.92 (m, 1H), 3.54 (s, 3H), 3.50 (m, 1H), 2.93 (dd, J=12.3 and 11.0 Hz, 1H), 1.48(s, 6H), 1.44 (d, J=5.4 Hz, 3H), 1.01(d, J=6.0, 3H). MS: Calculated for C20H27NO7S (M−OH): 408.15. Found: 408.1.

Workup

  1. washwashed with water (5 times 10 mL) and brine (30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75a4b9ea2cdc42348551099dd183f4ae
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06387901B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes