Lithium Hydroxide → HCID 68858706, compound

HRID 1726437Notes

Reaction equation

HRID 1726437 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11](Cl)=[O:12].C([O:16][C:17]([C@@:19]12[CH2:37][C@H:36]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:27](=[O:46])[N:26]1[C@@H:22]([CH2:23][C@@H:24]([NH2:47])[CH2:25]1)[C:21](=[O:48])[NH:20]2)=[O:18])C.CCN(C(C)C)C(C)C.[OH-].[Li+]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CO.O>[C:42]([O:41][C:39]([NH:38][C@@H:28]1[C:27](=[O:46])[N:26]2[C@@H:22]([CH2:23][C@@H:24]([NH:47][C:11]([N:2]3[CH2:3][CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)=[O:12])[CH2:25]2)[C:21](=[O:48])[NH:20][C@@:19]2([C:17]([OH:18])=[O:16])[C@@H:36]([CH2:37]2)[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

9

Reactant 4

HCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 218905713,4-Dihydroisoquinoline-2(1H)-carbonyl chlorideHCID 66657256HCID 66657256, compound

Product 1

HCID 68858706HCID 68858706, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,4-dihydro-1H-isoquinoline-2-carbonyl chloride (0.030 g, 0.152 mmol), (1S,4R,6S,14S,18R)-18-amino-14-tert-butoxycarbonylamino-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid ethyl ester (0.025 g, 0.050 mmol), DIEA (0.027 ml, 0.153 mmol) and a catalytic amount of DMAP were stirred together in methylene chloride (0.3 ml) for 18 h. The reaction was placed onto silica gel and the product eluted with 40% acetone/hexanes and isolated as a white solid. The solid was dissolved in methanol and treated with lithium hydroxide (0.011 g, 0.254 mmol) and 1 drop of water. After stirring for 5 h, the reaction was diluted with methylene chloride (30 ml), washed with 1N aqueous HCl (30 ml), brine (30 ml), dried over magnesium sulfate and concentrated to give the title compound as a white solid. LCMS=624 (MH+).

Workup

  1. washthe product eluted with 40% acetone/hexanes
  2. customisolated as a white solid
  3. washwashed with 1N aqueous HCl (30 ml), brine (30 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f4e1440096ff41b991138d0acb57eecf
Source dataset
uspto-grants-2009_02
Patent number
US07491794B2

Reaction notes

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