Potassium Sulfate → HCID 58777908, compound

HRID 2099364Notes

Reaction equation

HRID 2099364 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][C@@H:7]([NH:12][CH2:13][C@H:14]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][N:15]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:8]([O:10]C)=[O:9])=[CH:4][CH:3]=1.O.[OH-].[Li+].S([O-])([O-])(=O)=O.[K+].[K+]>O1CCCC1.O>[C:27]([O:26][C:24]([N:15]1[C@@H:14]([CH2:13][NH:12][C@@H:7]([C:8]([OH:10])=[O:9])[CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:32][CH:31]=2)[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 24507Potassium SulfateHCID 168937Lithium hydroxide, monohydrate2×HCID 86760923HCID 86760923, compound

Product 1

HCID 58777908HCID 58777908, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

6.4 g of tert-butyl (3R)-3-({[(1R)-1-(4-chlorobenzyl)-2-methoxy-2-oxoethyl]amino}methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate are dissolved in 150 ml of a mixture of tetrahydrofuran/water/MeoH (1/1/1) at 0° C., and 0.99 g of lithium hydroxide hydrate is added. Stirring is maintained at 0° C. for 3 h. 0.5 g of lithium hydroxide hydrate is then added. The medium is maintained at 0° C. for 16 h. Potassium sulphate is added up to a pH of 7. The precipitate obtained is filter-dried and rinsed with diethyl ether. After drying over P2O5, 7.2 g of N-{[(3R)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl]methyl}-4-chloro-D-phenylalanine are obtained.

Workup

  1. temperatureThe medium is maintained at 0° C. for 16 h
  2. customThe precipitate obtained
  3. customis filter-dried
  4. washrinsed with diethyl ether
  5. dry with materialAfter drying over P2O5, 7.2 g of N-{[(3R)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl]methyl}-4-chloro-D-phenylalanine
  6. customare obtained

Sources & evidence

ORD record
ord-544b6de00c77482ea394406df09feb67
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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