Water → HCID 117599109, compound

HRID 522386Notes

Reaction equation

HRID 522386 reaction equation
[CH:1]1([C@H:6]2[C:38](=[O:39])[N:37]3[CH2:40][C@@H:34]([CH2:35][C@H:36]3[C:41](=[O:57])[NH:42][C@:43]3([C:48](=[O:56])[NH:49][S:50]([CH:53]4[CH2:55][CH2:54]4)(=[O:52])=[O:51])[CH2:45][C@H:44]3[CH:46]=[CH2:47])[O:33][C:18]3=[N:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]([O:27][CH2:28][C:29]([O:31]C)=[O:30])=[C:17]3[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][C@@H:11]3[CH2:58][CH2:59][CH2:60][C@H:10]3[O:9][C:8](=[O:61])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[Li+].[OH-]>C1COCC1.CO>[CH:1]1([C@H:6]2[C:38](=[O:39])[N:37]3[CH2:40][C@@H:34]([CH2:35][C@H:36]3[C:41](=[O:57])[NH:42][C@:43]3([C:48](=[O:56])[NH:49][S:50]([CH:53]4[CH2:54][CH2:55]4)(=[O:51])=[O:52])[CH2:45][C@H:44]3[CH:46]=[CH2:47])[O:33][C:18]3=[N:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:17]3[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][C@@H:11]3[CH2:58][CH2:59][CH2:60][C@H:10]3[O:9][C:8](=[O:61])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 131735530HCID 131735530, compound

Product 1

HCID 117599109HCID 117599109, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1 (43 mg) was dissolved in THF (1 ml) and methanol (0.2 ml). Water (0.5 ml) and LiOH (11.95 mg) were added and the reaction was stirred until complete conversion. The reaction was quenched with 1N HCl (0.4 mL) and 5% KHSO4 was added until the pH was 3. The mixture was extracted with ether then ethyl acetate. The combined organics were washed with water (5×) then brine, dried over magnesium sulfate, filtered and concentrated to yield 42 mg of pure product. HRMS (ES+) m/z 848.3522 (M+H)+.

Workup

  1. customThe reaction was quenched with 1N HCl (0.4 mL) and 5% KHSO4
  2. additionwas added until the pH was 3
  3. extractionThe mixture was extracted with ether
  4. washThe combined organics were washed with water (5×)
  5. dry with materialbrine, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8328fd4c6b1f42f7a4fd9ae1e0d84b70
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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