3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR, 5aS, 8aS, 8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester → 3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3r, 4s, 5r)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester

HRID 1008120Notes

Reaction equation

HRID 1008120 reaction equation
CC1(C)[O:37][C@H:5]2[O:6][CH:7]([CH2:15][O:16][C:17]([N:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)/[C:21](=[CH:28]/[C:29]4[NH:30][C:31]([CH3:35])=[CH:32][C:33]=4[CH3:34])/[C:20]3=[O:36])=[O:18])[C@@H:8]3[O:12]C(C)(C)[O:10][C@@H:9]3[C@H:4]2[O:3]1>Cl.C1COCC1>[OH:12][C@@H:8]1[C@H:9]([OH:10])[C@@H:4]([OH:3])[CH:5]([OH:37])[O:6][CH:7]1[CH2:15][O:16][C:17]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)/[C:21](=[CH:28]/[C:29]2[NH:30][C:31]([CH3:35])=[CH:32][C:33]=2[CH3:34])/[C:20]1=[O:36])=[O:18]

Participants

4

Reactant 1

HCID 1317245993-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR, 5aS, 8aS, 8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester

Product 1

HCID 601112343-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3r, 4s, 5r)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[1-(3,5-Dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR, 5aS, 8aS, 8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4′,5′-d]pyran-5-ylmethyl ester was dissolved in the mixture of 5.0 mL of 6 N HCl aq. and 20 mL of THF. The resultant mixture was stirred at room temperature for 3 h and 40° C. for 1 h and concentrated. The residue was washed with ethyl acetate and THF and dried to give 133 mg (60%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3R, 4S, 5R)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethyl ester as a yellow solid.

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with ethyl acetate and THF
  3. customdried

Sources & evidence

ORD record
ord-d0f6d6f1fdee4ed186bc1e0b1d82fc52
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

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