Lithium Hydroxide → HCID 11014769, compound

HRID 1198064Notes

Reaction equation

HRID 1198064 reaction equation
C[O:2][C:3](=[O:30])[C@@:4]([CH3:29])([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:5][C:6]([O:8][CH:9]1[CH:16]2[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:18][CH:10]1[CH2:11]3)[CH2:15]2)=[O:7].[Li+].[OH-]>O1CCOCC1>[CH:10]12[CH2:18][CH:14]3[CH2:13][CH:12]([CH2:17][CH:16]([CH2:15]3)[CH:9]1[O:8][C:6]([NH:5][C@@:4]([CH3:29])([C:3]([OH:30])=[O:2])[CH2:19][C:20]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=1)=[O:7])[CH2:11]2

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 14802502N-[(2-Adamantyloxy)carbonyl]-alpha-methyl-D-tryptophan methyl ester

Product 1

HCID 11014769HCID 11014769, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-[(2-adamantyloxy)-carbonyl]α-methyl-D-tryptophan methyl ester (1.36 g, 3.3 mmol) in aqueous 1,4-dioxan (1:2) (20 mL) was added an excess of LiOH (0.210 g, 5 mmol) and stirred at room temperature overnight. After removing the solvent in vacuo the residue was chromatographed using 5% MeOH: 95% CH2Cl2 then 10% MeOH:90% CH2Cl2 as eluants to yield the acid (0.953 mg, 90%) as a white solid, crystallized from n-hexane, mp 210°-215° C. (EtOAc/n-hexane); IR (film) 1689 cm-1 ; NMR (CDCl3 -D2O), δ 1.3--2.2 (14H, m), 1.70 (3H, s), 3.26 (1H, d, J 1.35 Hz), 3.63 (1H, d, 13.5 Hz); 4.77 (1H, br.s), 6.85-7.60 (5H, m).

Workup

  1. customAfter removing the solvent in vacuo the residue
  2. customwas chromatographed

Sources & evidence

ORD record
ord-70c2d05e1c234682af2f81aa9d97e311
Source dataset
uspto-grants-1994_01
Patent number
US05278316

Reaction notes

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