Lithium Hydroxide → HCID 58257042, compound

HRID 1915971Notes

Reaction equation

HRID 1915971 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][C:6](=[O:72])[CH:7]([NH:11][C:12](=[O:71])[C@H:13]([NH:35][C:36]([C:38]1([NH:41][C:42](=[O:70])[CH2:43][C@H:44](O)/[CH:45]=[CH:46]/[CH2:47][CH2:48][S:49][C:50]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:40][CH2:39]1)=[O:37])[CH2:14][S:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:8]([CH3:10])[CH3:9].[Li+].[OH-:75].CC1C=CC=C([N+]([O-])=O)C=1C(OC(C1C([N+]([O-])=O)=CC=CC=1C)=O)=O>C1COCC1.O.CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:8]([CH:7]1[NH:11][C:12](=[O:71])[C@@H:13]([CH2:14][S:15][C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH:35][C:36](=[O:37])[C:38]2([CH2:39][CH2:40]2)[NH:41][C:42](=[O:70])[CH2:43][C@@H:44](/[CH:45]=[CH:46]/[CH2:47][CH2:48][S:49][C:50]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[O:75][C:3](=[O:2])[CH2:4][NH:5][C:6]1=[O:72])([CH3:10])[CH3:9]

Participants

8

Reactant 3

HCID 3939Lithium HydroxideHCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 58257035HCID 58257035, compound

Product 1

HCID 58257042HCID 58257042, compoundYield 50%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4 (171 mg, 0.17 mmol, 1 eq) in THF (6 mL) at 0° C. was added a solution of LiOH (6.0 mg, 0.25 mmol, 1.5 eq) in H2O (2 mL) dropwise. The mixture was stirred for 2 h, then quenched with 1N HCl (2 mL) and brine (10 mL). The organic layer was separated and the resulting aqueous layer was further extracted with EtOAc (2×15 mL) and CH2Cl2 (15 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The resulting carboxylic acid was then dried under high vacuum for 2 h, To a solution of MNBA (69 mg, 0.21 mmol, 1.2 eq) and DMAP (49.3 mg, 0.40 mmol, 2.4 eq) in CH2Cl2 (150 mL) was added a solution of the crude carboxylic acid in CH2Cl2 (60 mL) and THF (10 mL) dropwise over 3 h. The reaction mixture was then left to stir at rt overnight. The solvent was then removed in vacuo and the residue was further purified by silica gel column chromatography with hexane/EtOAc (2:3) to yield 5 as a white solid (83 mg, 50%).

Workup

  1. customquenched with 1N HCl (2 mL) and brine (10 mL)
  2. customThe organic layer was separated
  3. extractionthe resulting aqueous layer was further extracted with EtOAc (2×15 mL) and CH2Cl2 (15 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. waitThe reaction mixture was then left
  7. stirringto stir at rt overnight
  8. customThe solvent was then removed in vacuo
  9. customthe residue was further purified by silica gel column chromatography with hexane/EtOAc (2:3)

Sources & evidence

ORD record
ord-e7bd76f7d9134c79b55c586a74d8f541
Source dataset
uspto-grants-2013_12
Patent number
US08614193B2

Reaction notes

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