HCID 69627447, compound → HCID 22237432, compound

HRID 324094Notes

Reaction equation

HRID 324094 reaction equation
C([O:5][C:6](=[O:45])[CH2:7][O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[CH:13][C:12]([C:22](=[O:37])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:11][C:10]=1[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[CH:39]=1)(C)(C)C>C(O)=O>[CH3:21][C:17]1[CH:16]=[C:15]([C:14]2[CH:13]=[C:12]([C:22](=[O:37])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:11]=[C:10]([C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[CH:39]=3)[C:9]=2[O:8][CH2:7][C:6]([OH:45])=[O:5])[CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 69627447HCID 69627447, compound

Product 1

HCID 22237432HCID 22237432, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of [3,3″-Dimethyl-5′-(7-phenyl-heptylcarbamoyl)-[1,1′:3′,1″]terphenyl-2′-yloxy]acetic acid tert-butyl ester (180 mg, 0.311 mmol) in 3.5 mL HCOOH was stirred at room temperature until all of the ester was consumed by TLC (1:1 EtOAc:Hexanes). The excess HCOOH was removed in vacuo (first on a rotoevaporator then pumping under high vacuum) then crystallized from CH2Cl2/Hexanes to yield 170 mg, 100% of the acid as a yellow foam. mp 58-62° C.; 1H NMR (DMSO-d6) δ1.21-1.28 (m, 6H); 1.44-1.57 (m, 4H); 2.35 (s, 6H); 2.53 (t, J=7.69 Hz, 2H); 3.23 (quartet, J=6.37 Hz, 2H); 3.82 (s, 2H); 7.10-7.24 (m, 7H); 7.30-7.41 (m, 6H); 7.80 (s, 2H); 8.51 (t, J=5.49 Hz, 1H); 12.60 (bs, 1H); IR 3375, 3025, 2925, 2865, 1730, 1630, 1600, 1550, 1450, 1350, 1210, 1195, 1080, and 700 cm−1; mass spectrum [(−)ESI], m/z 548 [M−H]−; Anal Calcd. for C36H39NO4: C, 78.66: H, 7.15; N, 2.55; Found: C, 77.39; H, 7.42; N, 2.37.

Workup

  1. customwas consumed by TLC (1:1 EtOAc:Hexanes)
  2. customThe excess HCOOH was removed in vacuo (first on a rotoevaporator
  3. customthen crystallized from CH2Cl2/Hexanes

Sources & evidence

ORD record
ord-76736454e5af4d1cab39085b211c5671
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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