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Triethylamine → Levodopa

HRID 389797
Notes
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Reaction equation

HRID 389797 reaction equation
C([NH:8][C@@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])(OC(C)(C)C)=O.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl.CN(C=O)C.C(OCC)C>[O:11]=[C:10]([C@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[NH2:8])[OH:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14217229N-(tert-Buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine

Product 1

HCID 6047Levodopa

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Procedure

2.1 g of p(EG1k-Asp) (1.77 mmol —NH2) was dissolved in 30 mL of DCM and 15 mL of DMF. 842 mg of N-Boc-DOPA (2.83 mmol), 382 mg of HOBt (2.83 mmol), HBTU (2.83 mmol), and 595 μL of Et3N (4.25 mmol) were added. The mixture was stirred for 1 hr at room temperature and added to 450 mL ethyl ether. The polymer was further precipitated in cold MeOH and dried in vacuum to yield 1.9 g of PEE-1 (GPC: Mw=33,800, PD=1.3; UV-vis: 7.7±1.3 wt % DOPA).

Workup

  1. customThe polymer was further precipitated in cold MeOH
  2. customdried in vacuum

Sources & evidence

ORD record
ord-e2321beafadf4242989305f3aace3add
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383092B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes