Methanol → 1-isobutyl-3-[2-[4-[3-[4-[[4-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]indol-3-yl]methyl]phenoxy]propyl]-4,9-diazaspiro[5.5]undecan-9-yl]-2-oxo-ethyl]urea

HRID 2284879Notes

Reaction equation

HRID 2284879 reaction equation
C([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12]C(=O)C)[C@H:10]([O:16]C(=O)C)[C@@H:9]([O:20]C(=O)C)[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH2:44][N:45]4[CH2:50][C:49]5([CH2:55][CH2:54][N:53]([C:56](=[O:66])[CH2:57][NH:58][C:59](=[O:65])[NH:60][CH2:61][CH:62]([CH3:64])[CH3:63])[CH2:52][CH2:51]5)[CH2:48][CH2:47][CH2:46]4)=[CH:37][CH:36]=3)=[CH:25]2)[O:7]1)(=O)C.CO.C[O-].[Na+]>O>[CH2:61]([NH:60][C:59]([NH:58][CH2:57][C:56]([N:53]1[CH2:54][CH2:55][C:49]2([CH2:48][CH2:47][CH2:46][N:45]([CH2:44][CH2:43][CH2:42][O:41][C:38]3[CH:37]=[CH:36][C:35]([CH2:34][C:26]4[C:27]5[C:32](=[CH:31][CH:30]=[CH:29][C:28]=5[CH3:33])[N:24]([C@H:8]5[C@H:9]([OH:20])[C@@H:10]([OH:16])[C@H:11]([OH:12])[C@@H:6]([CH2:5][OH:4])[O:7]5)[CH:25]=4)=[CH:40][CH:39]=3)[CH2:50]2)[CH2:51][CH2:52]1)=[O:66])=[O:65])[CH:62]([CH3:64])[CH3:63]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 118045058[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[3-[9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]undecan-4-yl]propoxy]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate

Product 1

HCID 917550101-isobutyl-3-[2-[4-[3-[4-[[4-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]indol-3-yl]methyl]phenoxy]propyl]-4,9-diazaspiro[5.5]undecan-9-yl]-2-oxo-ethyl]ureaYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cool a mixture of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[3-[9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]undecan-4-yl]propoxy]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (74.28 mmoles; 68.20 g) and methanol (341.00 mL) in an ice-bath. Add sodium methoxide (111.43 mmoles; 6.02 g). Stir the mixture for 10 minutes. Pour the mixture into water (3.5 L), then filter the mixture. Wash the solid with water, dry on the sinter, and further dry in a vacuum oven at 60° C. to give the title compound (49.8 g, 89% yield) mass spectrum (m/z): 750.6 (M+1).

Workup

  1. temperatureCool
  2. filtrationfilter the mixture
  3. washWash the solid with water
  4. customdry on the sinter
  5. customfurther dry in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-cbd39ad7da4f495dbb6ca731beec257e
Source dataset
uspto-grants-2015_09
Patent number
US09145437B2

Reaction notes

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