Hydrochloric Acid → Boc-Gly Rotigotine

HRID 389795Notes

Reaction equation

HRID 389795 reaction equation
[CH3:1][CH2:2][CH2:3][N:4]([C@@H:12]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:15]=2[CH2:14][CH2:13]1)[CH2:5][CH2:6][C:7]1[S:11][CH:10]=[CH:9][CH:8]=1.Cl.[CH3:24][C:25]([O:28][C:29]([NH:31][CH2:32][C:33]([OH:35])=[O:34])=[O:30])([CH3:27])[CH3:26].C1CCC(N=C=NC2CCCCC2)CC1.Cl>ClCCl.CN(C1C=CN=CC=1)C.C(OCC)C>[NH:31]([C:29]([O:28][C:25]([CH3:27])([CH3:26])[CH3:24])=[O:30])[CH2:32][C:33]([OH:35])=[O:34].[CH3:1][CH2:2][CH2:3][N:4]([C@@H:12]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:15]=2[CH2:14][CH2:13]1)[CH2:5][CH2:6][C:7]1[S:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 180335Rotigotine hydrochloride

Product 1

HCID 131730238Boc-Gly Rotigotine

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Rotigotine HCl (1.2 g, 3.41 mmol) and Boc-Glycine-OH (1.195 g, 6.82 mmol) were dissolved in dichloromethane (150 ml) to give a suspension. After addition of DMAP (0.625 g, 5.11 mmol) and DCC (1.407 g, 6.82 mmol), the mixture was stirred for 16 hours at room temperature. The mixture was filtered using filter paper and the filtrate was quenched with 51 mL of 0.1 N HCl (5.11 mmol). The layers were separated and the aqueous phase was extracted with 7 mL of dichloromethane. The combined organic phases were washed with water and then with brine, dried over Na2SO4, filtered, concentrated using a rotary evaporator, and dried in vacuo to give a crude pale yellow solid. The crude material was stirred with diethyl ether (50 mL) for 30 minutes, filtered on a glass frit, washed with diethyl ether, and dried in vacuo to give a pale yellow powder Boc-Gly-Rotigotine.HCl (1.258 g, 75% yield).

Workup

  1. customto give a suspension
  2. filtrationThe mixture was filtered
  3. filtrationusing filter paper
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with 7 mL of dichloromethane
  6. washThe combined organic phases were washed with water
  7. dry with materialwith brine, dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customa rotary evaporator
  11. customdried in vacuo
  12. customto give a crude pale yellow solid
  13. filtrationfiltered on a glass frit
  14. washwashed with diethyl ether
  15. customdried in vacuo

Sources & evidence

ORD record
ord-eb3a6acec1f4434881e45c5545151c3a
Source dataset
uspto-grants-2013_02
Patent number
US08383093B1

Reaction notes

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