Lithium Hydroxide → HCID 86653404, compound

HRID 1915973Notes

Reaction equation

HRID 1915973 reaction equation
C[O:2][C:3](=[O:70])[CH2:4][NH:5][C:6]([C:8]1([NH:11][C:12](=[O:69])[C@H:13]([NH:35][C:36](=[O:68])[CH2:37][NH:38][C:39](=[O:67])[CH2:40][C@H:41]([OH:66])/[CH:42]=[CH:43]/[CH2:44][CH2:45][S:46][C:47]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:14][S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7].[Li+].[OH-]>C1COCC1.O>[OH:66][C@H:41](/[CH:42]=[CH:43]/[CH2:44][CH2:45][S:46][C:47]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH2:40][C:39]([NH:38][CH2:37][C:36]([NH:35][C@H:13]([CH2:14][S:15][C:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:12]([NH:11][C:8]1([C:6]([NH:5][CH2:4][C:3]([OH:70])=[O:2])=[O:7])[CH2:10][CH2:9]1)=[O:69])=[O:68])=[O:67]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86653405HCID 86653405, compound

Product 1

HCID 86653404HCID 86653404, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4 (157.3 mg, 0.154 mmol) in THF (2.45 mL) at 0° C. was added LiOH (9.19 mg, 0.384 mmol) in water (0.65 mL) dropwise and the reaction was stirred for 55 min. The reaction mixture was then quenched with 1M HCl (aq) (10 mL) and diluted with water (10 mL). EtOAc (30 mL) was added the layers separated and the aqueous layer was extracted with EtOAc (3×30 mL). The organic layers were combined, washed with saturated brine (20 mL), separated, dried (MgSO4) and concentrated in vacuo to give 5 (153 mg, 0.154 mmol, 100%) as a white solid, which was used without further purification [MS (ES−) 959.2 (100%, [M−H]−)].

Workup

  1. customThe reaction mixture was then quenched with 1M HCl (aq) (10 mL)
  2. additiondiluted with water (10 mL)
  3. additionEtOAc (30 mL) was added the layers
  4. customseparated
  5. extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
  6. washwashed with saturated brine (20 mL)
  7. customseparated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e72970ab29b74f05aa92a6c2857ecd06
Source dataset
uspto-grants-2013_12
Patent number
US08614193B2

Reaction notes

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