Hydrochloric Acid → HCID 131731855, compound

HRID 74805Notes

Reaction equation

HRID 74805 reaction equation
[CH:1]1([CH2:8][CH2:9][NH:10][C:11](=[O:58])[C@H:12]([CH3:57])[C@H:13]([C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:56])[CH2:22][C@@H:23]([O:54][CH3:55])[C@@H:24]([N:29]([CH3:53])[C:30](=[O:52])[C@@H:31]([NH:35][C:36]([C@@:38]2([CH3:51])[CH2:43][CH2:42][CH2:41][CH2:40][N:39]2C(OC(C)(C)C)=O)=[O:37])[CH:32]([CH3:34])[CH3:33])[C@@H:25]([CH3:28])[CH2:26][CH3:27])[O:14][CH3:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=[CH:2]1.[ClH:59]>O1CCOCC1>[ClH:59].[CH:1]1([CH2:8][CH2:9][NH:10][C:11](=[O:58])[C@H:12]([CH3:57])[C@H:13]([C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](=[O:56])[CH2:22][C@@H:23]([O:54][CH3:55])[C@@H:24]([N:29]([CH3:53])[C:30](=[O:52])[C@@H:31]([NH:35][C:36]([C@@:38]2([CH3:51])[CH2:43][CH2:42][CH2:41][CH2:40][NH:39]2)=[O:37])[CH:32]([CH3:34])[CH3:33])[C@@H:25]([CH3:28])[CH2:26][CH3:27])[O:14][CH3:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89582365HCID 89582365, compound

Product 1

HCID 131731855HCID 131731855, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to the general procedure C, from #179 (162 mg, 0.199 mmol, 1 eq.) and 4M solution of hydrochloric acid in dioxane (2.0 mL) was synthesized the desired material as a gum (155 mg). A portion of this gum (25 mg) was azeotroped with a 1/1 mixture of methanol/acetonitrile to afford #180 (20 mg, 83%) as a solid. 1H NMR (400 MHz, DMSO-d6), δ 9.02-9.13 (m), 8.83-8.93 (m), 8.39-8.46 (m), 8.00-8.06 (m), 7.78 (t), 7.24-7.30 (m), 7.16-7.21 (m), 6.54-6.65 (m), 6.09-6.19 (m), 5.11-5.18 (m), 4.69-4.78 (m), 4.59-4.68 (m), 4.46-4.56 (m), 4.08-4.13 (m), 3.95-4.03 (m), 3.77-3.85 (m), 3.54-3.73 (m), 3.43-3.53 (m), 3.37-3.42 (m), 3.24-3.33 (m), 3.16-3.22 (m), 3.03-3.15 (m), 2.99-3.02 (m), 2.89-2.98 (m), 2.65-2.76 (m), 2.41-2.54 (m), 2.15-2.39 (m), 2.07-2.15 (m), 1.51-1.94 (m), 1.49 (d), 1.38 (t), 1.20-1.32 (m), 1.02-1.09 (m), 0.84-0.97 (m), 0.73-0.81 (m). LC-MS (Protocol Q1): m/z 714.6 [M+H+], retention time=0.76 HPLC (Protocol U): m/z 714.4 [M+H+], retention time=7.409 minutes (purity=90%).

Workup

  1. customA portion of this gum (25 mg) was azeotroped with a 1/1 mixture of methanol/acetonitrile

Sources & evidence

ORD record
ord-2b9df4c9a2264febad87045d424c0b95
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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