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Triphenylphosphine → HCID 118307763, compound

HRID 718448
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Reaction equation

HRID 718448 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]([CH3:33])=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:35][C:36]1[S:37][CH:38]=[C:39]([CH2:41][CH2:42]O)[N:40]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:34])=[N:14][C:15]([CH3:33])=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:42][CH2:41][C:39]3[N:40]=[C:36]([CH3:35])[S:37][CH:38]=3)=[CH:28][CH:27]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH2:19]1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 198767392-(2-Methyl-1,3-thiazol-4-yl)ethan-1-olHCID 118314205(S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate

Product 1

HCID 118307763
HCID 118307763, compound
Yield 64.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate (25 mg, 0.053 mmol), 2-(2-methylthiazol-4-yl)ethanol (22.92 mg, 0.160 mmol) and Ph3P-resin (69.7 mg, 0.267 mmol) in THF (2 mL) was added DEAD (0.025 mL, 0.160 mmol) at rt. After 18 h, mixture was filtered to remove polymer, concentrated and treated with 1N NaOH (1.067 mL, 1.067 mmol) in MeOH (1 mL) at 75° C. for 16 h. Mixture was then cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-(2-(2-methylthiazol-4-yl)ethoxy)phenyl)pyridin-3-yl)acetic acid (19.4 mg, 0.034 mmol, 64.3% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.26-7.18 (m, 2H), 7.08-6.97 (m, 3H), 5.83 (s, 1H), 4.41-4.28 (m, 2H), 3.40-3.30 (m, 2H), 3.14 (t, J=6.4 Hz, 2H), 2.80 (t, J=12.1 Hz, 1H), 2.64 (s, 3H), 2.43 (s, 3H), 2.17 (d, J=11.0 Hz, 1H), 2.06 (s, 3H), 1.99-1.93 (m, 1H), 1.49 (br. s., 1H), 1.30 (br. s., 1H), 1.18 (d, J=11.4 Hz, 1H), 1.13 (s, 9H), 1.03 (d, J=10.6 Hz, 1H), 0.85 (br. s., 3H), 0.61 (br. s., 3H). LCMS (M+H)=566.6.

Workup

  1. filtrationmixture was filtered
  2. customto remove polymer
  3. concentrationconcentrated
  4. temperatureMixture was then cooled
  5. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-a1a17b3933eb4bd9b2271921e8c20f2c
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193720B2

Reaction notes

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