Sodium Hydroxide → HCID 118318869, compound

HRID 921220Notes

Reaction equation

HRID 921220 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:43]([CH3:44])=[N:42][C:41]2=[CH:45][C:38]3=[N:39][N:40]2[C:13]=1[N:14]1[CH2:48][CH2:47][C:17]([CH3:49])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([CH3:46])[O:24][C:25]2[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=4[CH:32]=[CH:33][C:34]=2[CH2:35][O:36][CH2:37]3)[CH2:16][CH2:15]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:43]([CH3:44])=[N:42][C:41]2=[CH:45][C:38]3=[N:39][N:40]2[C:13]=1[N:14]1[CH2:15][CH2:16][C:17]([CH3:49])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C@H:23]([CH3:46])[O:24][C:25]2[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=4[CH:32]=[CH:33][C:34]=2[CH2:35][O:36][CH2:37]3)[CH2:47][CH2:48]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118318870HCID 118318870, compound

Product 1

HCID 118318869HCID 118318869, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl (2S)-2-(tert-butoxy)-2-[(24S)-4,24,30-trimethyl-11,23,29-trioxa-1,5,7,8-tetraazahexacyclo[28.2.2.16,9.02,7.013,22.016,21]pentatriaconta-2,4,6(35),8,13(22),14,16(21),17,19-nonaen-3-yl]acetate (47 mg, 0.070 mmol) and NaOH (0.070 mL, 0.070 mmol) in EtOH (2 mL) was refluxed for 2 h. It was then cooled to rt and purified by preparative HPLC to obtain (2S)-2-(tert-butoxy)-2-[(24S)-4,24,30-trimethyl-11,23,29-trioxa-1,5,7,8-tetraazahexacyclo[28.2.2.16,9.02,7.013,22.016,21]pentatriaconta-2,4,6(35),8,13(22),14,16(21),17,19-nonaen-3-yl]acetic acid (31.3 mg, 0.046 mmol, 66.0% yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.12 (d, J=8.4 Hz, 1H), 7.87 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 7.53-7.43 (m, 3H), 6.58 (s, 1H), 5.82 (s, 1H), 4.83-4.75 (m, 2H), 4.75-4.67 (m, 1H), 4.58 (d, J=10.6 Hz, 1H), 4.49-4.35 (m, 2H), 3.74 (t, J=10.8 Hz, 1H), 3.37-3.53 (m, 2H), 3.06 (d, J=9.2 Hz, 1H), 2.64 (d, J=11.7 Hz, 1H), 2.50 (s, 3H), 1.95 (d, J=13.2 Hz, 2H), 1.88-1.45 (m, 8H), 1.20 (s, 3H), 1.16 (s, 9H), 1.07 (d, J=5.9 Hz, 3H). LCMS (M+1)=645.3.

Workup

  1. temperaturewas refluxed for 2 h
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-498e13d58d404613a6555a83612d7c34
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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