Sodium Hydroxide → HCID 15942362, compound

HRID 2360638Notes

Reaction equation

HRID 2360638 reaction equation
C1([O:6][C:7](=[O:39])[C@@H:8]([NH:15][C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27](=[O:38])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](=[O:37])[NH:35][OH:36])[CH:21]=2)=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)CCCC1.[OH-].[Na+]>C1COCC1>[OH:36][NH:35][C:34]([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:27]([NH:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][NH:18][C:16](=[O:17])[NH:15][C@@H:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:7]([OH:39])=[O:6])=[O:38])=[O:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15942361HCID 15942361, compound

Product 1

HCID 15942362HCID 15942362, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound (79) (75 mg) was dissolved in THF (1 ml) and 2M NaOH (aq, 1 ml) added. The reaction was stirred at room temperature for 2 h. THF was removed under a stream of N2 and the aqueous layer (˜1 ml) was purified by preparative HPLC to yield compound (80). LCMS purity 99%, m/z 471 [M++H]+, 1H NMR (400 MHz, MeOD), δ: 1.20-1.35 (4H, m, 2×CH2), 1.45-1.65 (4H, m, 2×CH2), 2.00 (2H, t, CH2), 2.25 (2H, t, CH2), 4.20 (2H, s CH2NH), 5.25 (1H, s CHPh), 6.90 (1H, d, Ar), 7.10 (1H, t, Ar), 7.15-7.40 (7H, m, Ar).

Workup

  1. customTHF was removed under a stream of N2
  2. customthe aqueous layer (˜1 ml) was purified by preparative HPLC

Sources & evidence

ORD record
ord-ca9f5092e0f44aa1a0683d199a211399
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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