HCID 49837481, compound → HCID 86616576, compound

HRID 556223Notes

Reaction equation

HRID 556223 reaction equation
[OH:1][CH:2]1[C:18]([CH3:20])([CH3:19])[C:17](=[O:21])[CH:16]([CH3:22])[CH:15]([OH:23])[CH:14]([CH3:24])[CH2:13][CH2:12][CH2:11][CH:10]2[CH:8]([N:9]2[CH2:25][CH2:26][OH:27])[CH2:7][CH:6]([C:28]([CH3:36])=[CH:29][C:30]2[N:31]=[C:32]([CH3:35])[S:33][CH:34]=2)[O:5][C:4](=[O:37])[CH2:3]1.[C:38](=O)([O:49][CH2:50][CH2:51][S:52][S:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1)[O:39]N1C2C=CC=CC=2N=N1>ClCCl.CN(C1C=CN=CC=1)C>[C:38](=[O:39])([O:49][CH2:50][CH2:51][S:52][S:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=1)[O:27][CH2:26][CH2:25][N:9]1[C@@H:8]2[C@H:10]1[CH2:11][CH2:12][CH2:13][C@H:14]([CH3:24])[C@H:15]([OH:23])[C@@H:16]([CH3:22])[C:17](=[O:21])[C:18]([CH3:19])([CH3:20])[C@@H:2]([OH:1])[CH2:3][C:4](=[O:37])[O:5][C@H:6](/[C:28](/[CH3:36])=[CH:29]/[C:30]1[N:31]=[C:32]([CH3:35])[S:33][CH:34]=1)[CH2:7]2

Participants

5

Reactant 2

HCID 49837481HCID 49837481, compoundHCID 74065034HCID 74065034, compound2×

Product 1

HCID 86616576HCID 86616576, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [1S-[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]]-7,11-Dihydroxy-17-[2-hydroxyethyl]-8,8,10,12-tetramethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4-oxa-17-azabicyclo[14.1.0]heptadecane-5,9-dione in anhydrous dichloromethane at 0° C. was added DMAP (1.2 eq.) and benzo[d][1,2,3]triazol-1-yl 2-(2-(pyridin-2-yl)disulfanyl)ethyl carbonate (1.0 eq.) in tandem. The reaction mixture was stirred at 0° C. under argon and monitored by TLC every 10 min. Additional DMAP (1.2 eq.) and Compound I (2)(1.0 eq.) were added as necessary until all of Compound G was consumed. The reaction was quenched with MeOH (1 mL) at 0° C., the solvent was removed under vacuum, and the residue was purified by chromatography (silica gel, 2.5-5% MeOH in DCM) to afford the title compound as a beige solid. Compound amounts and recoveries are listed below in Table 3. Total yield from 2.95 g of Compound G was 2.80 g (67.9%) of Compound I.

Workup

  1. customwas consumed
  2. customThe reaction was quenched with MeOH (1 mL) at 0° C.
  3. customthe solvent was removed under vacuum
  4. customthe residue was purified by chromatography (silica gel, 2.5-5% MeOH in DCM)

Sources & evidence

ORD record
ord-e2a283956b694482b159ac2426b0e6bd
Source dataset
uspto-grants-2011_11
Patent number
USRE042930E1

Reaction notes

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