2,3-Dihydroxybutanedioic Acid → HCID 46893929, compound

HRID 1944028Notes

Reaction equation

HRID 1944028 reaction equation
[N:1]([CH:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]([O:20]CC)=[O:19])[C:7]=2[CH2:6][CH2:5]1)=[N+:2]=[N-:3].[CH2:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:24]#[CH:25].C(O)(C(O)=O)C(O)C(O)=O>>[CH2:23]([C:24]1[N:1]([CH:4]2[CH2:16][C:15]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[N:8]([CH2:17][C:18]([OH:20])=[O:19])[C:7]=3[CH2:6][CH2:5]2)[N:2]=[N:3][CH:25]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 575753BenzylacetyleneHCID 59487221HCID 59487221, compound

Product 1

HCID 46893929HCID 46893929, compound

Procedure

The title compound was prepared using procedures described in EXAMPLE 7, Step 5 to 8 from ethyl (3-azido-1,2,3,4-tetrahydro-9H-carbazol-9-yl)acetate (J. Med. Chem., 2005, 48, 897) and prop-2-yn-1-ylbenzene. The resulting racemic acid was resolved by HPLC using a 4.6×250 mm Chiralcel OD column eluting with 40% MeOH, 30% iPrOH, 29.75% Hexanes and 0.25% Et3N at 1 mL/min and 254 nm (retention times=8.9 and 18.3 min) to afford EXAMPLE 9.1 and 9.2 respectively. 1H NMR of EXAMPLE 9.1: 1H NMR (400 MHz, DMSO-d6): δ 12.99 (s, 1H), 7.53 (s, 1H), 7.39-7.29 (m, 4H), 7.31-7.21 (m, 3H), 7.08 (dd, 1H), 6.99 (t, 1H), 4.95-4.84 (m, 2H), 4.75 (s, 1H), 4.22 (s, 2H), 3.20-3.08 (m, 1H), 3.00 (dd, 1H), 2.86 (dd, 1H), 2.79-2.64 (m, 1H), 2.36-2.27 (m, 1H), 2.05-1.95 (m, 1H). MS (+ESI) m/z: 387.1.

Workup

  1. washeluting with 40% MeOH, 30% iPrOH, 29.75% Hexanes and 0.25% Et3N at 1 mL/min and 254 nm (retention times=8.9 and 18.3 min)
  2. customto afford EXAMPLE 9.1 and 9.2 respectively

Sources & evidence

ORD record
ord-f091e850c38243fcb2c0860d5fa96b9d
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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