Hydrochloric Acid → HCID 54209855, compound

HRID 267085Notes

Reaction equation

HRID 267085 reaction equation
FC(F)(F)C(O)=O.C[O:9][C:10](=[O:48])[C@H:11]([CH2:44][CH2:45][S:46][CH3:47])[NH:12][C:13](=[O:43])[CH2:14][N:15]([CH2:27][C@@H:28]([NH:33][C:34](=[O:42])[C@@H:35]1[CH2:39][CH2:38][C:37](=[O:40])[N:36]1[CH3:41])[C@@H:29]([CH3:32])[CH2:30][CH3:31])[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.[Li+].[OH-].Cl>CO>[CH3:41][N:36]1[C:37](=[O:40])[CH2:38][CH2:39][C@H:35]1[C:34]([NH:33][C@@H:28]([C@@H:29]([CH3:32])[CH2:30][CH3:31])[CH2:27][N:15]([CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[CH2:14][C:13]([NH:12][C@H:11]([C:10]([OH:48])=[O:9])[CH2:44][CH2:45][S:46][CH3:47])=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67685010HCID 67685010, compound

Product 1

HCID 54209855HCID 54209855, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2(S)-((N-Methylpyroglutamyl)-amino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)-glycyl-methionine methyl ester trifluoroacetate salt (prepared in Example 25, 112 mg, 0.19 mmol) was dissolved in methanol (5 ml) and treated with 0.76 ml of 1N LiOH. The mixture was stirred for 4 hours at room temperature, then treated with 0.76 ml of 1N HCl. The solvent was evacuated in vacuo. The crude product was purified by preparative HPLC (Waters PrepPak C-18 eluting with CH3CN/0.1% TFA in H2O) to give, after lyophilization, the title compound.

Workup

  1. customThe solvent was evacuated in vacuo
  2. customThe crude product was purified by preparative HPLC (Waters PrepPak C-18 eluting with CH3CN/0.1% TFA in H2O)
  3. customto give

Sources & evidence

ORD record
ord-f59a14aa323146be9cc029c3d4bb6da5
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Reaction notes

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