Lithium Hydroxide → ((1S)-5-{3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 603432Notes

Reaction equation

HRID 603432 reaction equation
[CH2:1]([O:4][C:5]1[CH:30]=[C:29]([C:31]2S[C:33]3[CH2:39][CH2:38][CH2:37][CH2:36][C:34]=3[N:35]=2)[CH:28]=[CH:27][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C@H:17]([CH2:21][C:22]([O:24]CC)=[O:23])[CH2:16][CH2:15]2)[CH2:2][CH3:3].[OH-:40].[Li+]>C1COCC1.O.CO>[CH2:1]([O:4][C:5]1[CH:30]=[C:29]([C:31]2[O:40][C:33]3[CH2:39][CH2:38][CH2:37][CH2:36][C:34]=3[N:35]=2)[CH:28]=[CH:27][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C@H:17]([CH2:21][C:22]([OH:24])=[O:23])[CH2:16][CH2:15]2)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59300423ethyl ((1S)-5-{3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate

Product 1

HCID 67018940((1S)-5-{3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetic acidYield 53.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl ((1S)-5-{3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzthiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 166, 88.0 mg, 0.160 mmol) in THF/Water/Methanol (1:2:1) was added solid lithium hydroxide (38.4 mg, 1.60 mmol). The solution was stirred at rt for 3 h, and the solvent was then removed under reduced pressure. The residue was diluted with water and acidified using HCl (2 N aqueous solution) upon which a white precipitate formed. The solid was isolated by filtration to provide the title compound (43.5 mg, 52%) that did not require further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.37 (d, 1H), 7.32 (dd, 1H), 7.07 (d, 1H), 7.04 (d, 1H), 6.78 (s, 1H), 6.69 (dd, 1H), 4.15 (t, 2H), 4.11 (t, 2H), 3.96 (t, 2H), 3.33 (m, 1H), 2.61-2.85 (m, 7H), 2.2-2.30 (m, 3H), 2.11-2.19 (m, 2H), 1.58-1.84 (m, 7H), 0.98 (t, 3H); LC-MS: RT3.80 min, (M+H)+ 22.3.

Workup

  1. customthe solvent was then removed under reduced pressure
  2. additionThe residue was diluted with water
  3. customformed
  4. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-792d239c7f6f4d5e8793eacf49ea4966
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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