Hydrochloric Acid → 4-(4-{(1E)-4-[9-(aminoacetyl)-2,9-diazaspiro[5.5]undec-2-yl]but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside dihydrochloride

HRID 1625943Notes

Reaction equation

HRID 1625943 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:65][CH2:64][C:14]2([CH2:19][N:18]([CH2:20][CH2:21]/[CH:22]=[CH:23]/[C:24]3[CH:29]=[CH:28][C:27]([CH2:30][C:31]4[C:32]([O:39][C@@H:40]5[O:57][C@H:56]([CH2:58][O:59][C:60](=[O:62])[CH3:61])[C@@H:51]([O:52][C:53](=[O:55])[CH3:54])[C@H:46]([O:47][C:48](=[O:50])[CH3:49])[C@H:41]5[O:42][C:43](=[O:45])[CH3:44])=[N:33][NH:34][C:35]=4[CH:36]([CH3:38])[CH3:37])=[C:26]([CH3:63])[CH:25]=3)[CH2:17][CH2:16][CH2:15]2)[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:67]>ClCCl>[ClH:67].[ClH:67].[C:43]([O:42][C@@H:41]1[C@@H:46]([O:47][C:48](=[O:50])[CH3:49])[C@H:51]([O:52][C:53](=[O:55])[CH3:54])[C@@H:56]([CH2:58][O:59][C:60](=[O:62])[CH3:61])[O:57][C@H:40]1[O:39][C:32]1[C:31]([CH2:30][C:27]2[CH:28]=[CH:29][C:24](/[CH:23]=[CH:22]/[CH2:21][CH2:20][N:18]3[CH2:17][CH2:16][CH2:15][C:14]4([CH2:64][CH2:65][N:11]([C:9](=[O:10])[CH2:8][NH2:7])[CH2:12][CH2:13]4)[CH2:19]3)=[CH:25][C:26]=2[CH3:63])=[C:35]([CH:36]([CH3:37])[CH3:38])[NH:34][N:33]=1)(=[O:45])[CH3:44]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131731669tert-butyl[2-(2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undec-9-yl)-2-oxoethyl]carbamate

Product 1

HCID 867625414-(4-{(1E)-4-[9-(aminoacetyl)-2,9-diazaspiro[5.5]undec-2-yl]but-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside dihydrochlorideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl[2-(2-{(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl}-2,9-diazaspiro[5.5]undec-9-yl)-2-oxoethyl]carbamate (12.10 g, 13.09 mmoles), dichloromethane (121.00 mL), and hydrogen chloride (4M in 1,4-dioxane; 16.37 mL, 65.47 mmoles) is stirred at ambient temperature for 4 hours. The mixture is concentrated under reduced pressure to provide the title compound (11.70 g; 99.6% yield). Mass spectrum (m/z): 824 (M+1 for free base).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a6e4927e5bf7402fbd412c9929e30476
Source dataset
uspto-grants-2014_07
Patent number
US08785404B2

Reaction notes

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