Hydrochloric Acid → HCID 118096926, compound

HRID 2171288Notes

Reaction equation

HRID 2171288 reaction equation
C(OC([N:8]1[C@H:20]([C:21]([OH:23])=[O:22])[CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:10]=2[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.CCN(CC)CC>O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]3[CH2:19][C@@H:20]([C:21]([OH:23])=[O:22])[NH:8][CH2:9][C:10]2=3)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-Dioxane2×HCID 118096920HCID 118096920, compound

Product 1

HCID 118096926HCID 118096926, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The acid 3 (18.9 g, 44.5 mmol), 4M HCl in 1,4-dioxane solution (56 mL, 222.7 mmol), and 1,4-dioxane (85 mL) stirred at RT overnight. The reaction diluted with water (200 mL) and neutralized to pH 7 with Et3N. Water (400 mL) was added and the mixture stirred for 30 min. The solid was collected by filtration and washed with water (300 mL) to afford the amino acid 4 (13.0 g, 90%) as a pale yellow powder. 1H NMR (300 MHz, DMSO-d6): δ 8.95 (br s, 1H), 7.48 (d, 1H), 7.39 (d, 1H), 7.14-6.99 (m, 6H), 5.33 (s, 2H), 4.24 (d, 1H), 4.08 (d, 1H), 3.63-3.58 (m, 1H), 3.17-3.10 (m, 1H), 2.86-2.81 (m, 1H); LC-MS [M+H+ 325].

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with water (300 mL)

Sources & evidence

ORD record
ord-16ce747bf5ea438eb42329f4683dd578
Source dataset
uspto-grants-2015_06
Patent number
US09051320B1

Reaction notes

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