Triethylamine → HCID 59013438, compound

HRID 1716968Notes

Reaction equation

HRID 1716968 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[O:18][C@@:17]3([C:26]4[C:21](=[CH:22][C:23]([Cl:37])=[C:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=5)[CH:25]=4)[CH2:20][O:19]3)[C@H:16]([OH:38])[C@@H:15]([OH:39])[C@@H:14]2[OH:40])(=O)=O)=CC=1.[CH3:41][N:42](Cl)[CH3:43].CCN(CC)CC>CN(C=O)C.O>[Cl:37][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][C:24]=1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=1)[C@:17]1([C@H:16]([OH:38])[C@@H:15]([OH:39])[C@H:14]([OH:40])[C@@H:13]([CH2:12][N:42]([CH3:43])[CH3:41])[O:18]1)[O:19][CH2:20]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 123122N-ChlorodimethylamineHCID 86616575HCID 86616575, compound

Product 1

HCID 59013438HCID 59013438, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-iso-propylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (15 mg, 0.025 mmol) and dimethylamino hydrochloride (48 mg, 0.588 mmol) in DMF (1 mL), was added Et3N (67 mg, 0.662 mmol). After being stirred for 24 h at 80° C., the reaction mixture was diluted with H2O and extracted 3× with AcOEt. The combined organic layers were washed with brine prior to drying over Na2SO4. The volatiles were removed under reduced pressure. The resulting residue was purified by preparative HPLC to yield 6 mg of title compound. 1H NMR (CD3OD, 300 MHz) δ 7.41 (s, 1H), 7.24 (s, 1H), 7.13 (s, 4H), 5.18 (d, J=13.5 Hz, 1H), 5.13 (d, J=13.5 Hz, 1H), 4.17-4.02 (m, 3H), 3.76-3.75 (m, 2H), 3.46-3.18 (m, 3H), 2.90-2.81 (m, 1H), 2.76 (s, 6H), 1.22 (d, J=6.9 Hz, 6H); MS ESI (m/z) 462 (M+1)+, calc. 461.

Workup

  1. extractionextracted 3× with AcOEt
  2. washThe combined organic layers were washed with brine
  3. dry with materialto drying over Na2SO4
  4. customThe volatiles were removed under reduced pressure
  5. customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7b48aab54f384083842f4f55f95d5a3a
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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