Triethylamine → HCID 68621280, compound

HRID 1244689Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:26](C(O)=O)[CH2:25][N:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:11]2[CH2:10]1)=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.C([N:49]([CH2:52]C)CC)C.[CH3:54][Si:55]([CH3:60])([CH3:59])[CH2:56][CH2:57][OH:58]>C1(C)C=CC=CC=1>[CH3:54][Si:55]([CH3:60])([CH3:59])[CH2:56][CH2:57][O:58][C:52](=[O:37])[NH:49][CH:26]1[CH2:25][N:12]2[CH2:13][CH2:14][C:15]3[C:20]([CH:11]2[CH2:10][CH:9]1[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=3

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (RS,RS,RS)-2-tert-butoxycarbonylamino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-3-carboxylic acid (Example 1c, 6.91 g, 17.0 mmol), diphenylphosphoryl azide (7.40 g, 25.6 mmol), triethylamine (1.72 g, 17.0 mmol), 2-(trimethylsilyl)-ethanol (30.2 g, 256 mmol) and toluene (40 mL) was heated 48 h at 80° C. under a gentle nitrogen stream. The reaction mixture was then concentrated in vacuo, the residue chromatographed (SiO2, CH2Cl2/MeOH/NH4OH 80:1:0.2), and the product fractions triturated in hexane/ethyl acetate 1:1 to afford the title compound (5.22 g, 59%). White solid, MS (ISP) 522.4 (M+H)+.

Workup

concentrationThe reaction mixture was then concentrated in vacuo
customthe residue chromatographed (SiO2, CH2Cl2/MeOH/NH4OH 80:1:0.2)
customthe product fractions triturated in hexane/ethyl acetate 1:1

Sources & evidence

ORD record: ord-80ad5ce4d2f547f38975a5c23d3cd867
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122555B2

Reaction notes

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