Methanol → HCID 131736690, compound

HRID 1482249Notes

Reaction equation

HRID 1482249 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([Cl:21])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.CO.C(N(C(C)C)CC)(C)C.[CH:33]1[C:45]2[CH:44]([CH2:46][O:47][C:48]([NH:50][C@H:51]([C:67](=[O:74])[N:68]3[CH2:73][CH2:72][CH2:71][CH2:70][CH2:69]3)[CH2:52][C:53]3[CH:58]=[CH:57][C:56]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][C:64]([OH:66])=[O:65])=[CH:55][CH:54]=3)=[O:49])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1>ClCCl>[CH:42]1[C:43]2[CH:44]([CH2:46][O:47][C:48]([NH:50][C@H:51]([C:67](=[O:74])[N:68]3[CH2:69][CH2:70][CH2:71][CH2:72][CH2:73]3)[CH2:52][C:53]3[CH:54]=[CH:55][C:56]([CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][C:64]([OH:66])=[O:65])=[CH:57][CH:58]=3)=[O:49])[C:45]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]=2[CH:39]=[CH:40][CH:41]=1.[CH:11]1[CH:10]=[CH:9][C:8]([C:7]([Cl:21])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 945242-Chlorotrityl chlorideHCID 89668315HCID 89668315, compound

Product 1

HCID 131736690HCID 131736690, compoundYield 223.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chlorotrityl chloride resin (1.07 mmol/g, 100-200 mesh, 1% DVB, manufactured by Chem-Impex, 3.00 g, 3.21 mmol) and dichloromethane (20 ml) were mixed, followed by shaking at room temperature. Dichloromethane was removed, after which methanol (0.52 ml, 12.85 mmol) and diisopropylethylamine (1.35 ml, 7.75 mmol) were added to a solution of (S)-6-(4-(2-((((9H-fluoren-9-yl)methoxy) carbonyl)amino)-3-oxo-3-(piperidin-1-yl)propyl)phenyl)hexanoic acid (Compound SP427) (0.91 g, 1.60 mmol) in dichloromethane (14 ml) and the resulting mixture was added to the resin, followed by shaking at room temperature for 5 minutes. The reaction solution was removed, after which methanol (4.2 ml) and diisopropylethylamine (1.4 ml) were added to dichloromethane (14 ml), and the resulting mixture was added, followed by shaking at room temperature for 2.5 hours. This reaction solution was removed, and dichloromethane (20 ml) was then placed, followed by shaking. Dichloromethane was removed, and dichloromethane (20 ml) was then placed again, followed by shaking. Dichloromethane was removed, and the resin was then dried under reduced pressure to afford the title compound (Compound SP428) (3.15 g).

Workup

  1. customDichloromethane was removed
  2. additionthe resulting mixture was added to the resin
  3. stirringby shaking at room temperature for 5 minutes
  4. customThe reaction solution was removed
  5. additionafter which methanol (4.2 ml) and diisopropylethylamine (1.4 ml) were added to dichloromethane (14 ml)
  6. additionthe resulting mixture was added
  7. stirringby shaking at room temperature for 2.5 hours
  8. customThis reaction solution was removed
  9. stirringby shaking
  10. customDichloromethane was removed
  11. stirringby shaking
  12. customDichloromethane was removed
  13. customthe resin was then dried under reduced pressure

Sources & evidence

ORD record
ord-9f89edc86b9e4e9d8e21caac17d34345
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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