Dichloromethane → HCID 22941032, compound

HRID 342116Notes

Reaction equation

C(OC([NH:8][CH2:9][CH:10]([NH:34][CH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])[CH2:14][C@@H:13]1[CH2:30][CH2:31][CH2:32][CH3:33])=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:54]>>[ClH:54].[ClH:54].[ClH:54].[NH2:8][CH2:9][CH:10]([NH:34][CH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])[CH2:14][C@@H:13]1[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 15390990HCID 15390990, compound

Product 1

HCID 22941032HCID 22941032, compound

Procedure

A solution of 1-(3-tert-butoxycarbonylamino-2-(2-naphthylmethylamino)prop-1-yl)-2(S)-butyl-4-(1-naphthoyl)piperazine (0.313 g, 0.514 mmol) in methylene chloride (10 mL) was deprotected with trifluoroacetic acid (5 mL) and converted to the free base (255 mg) according to the procedure described in Example 1, Step E. Purification of 40 mg by preparative HPLC used gradient elution with solvents A and B (from Example 1; 95% to 5% solvent A). Ion exchange and lyophilization as described furnished the title compound as a white solid. FAB ms (m+1) 509. Anal. Calc. for C33H40N4O.0.05 H2O 4.45 HCl: C, 59.00; H, 6.68; N, 8.34. Found: C, 59.00; H, 6.51; N, 8.44.

Workup

customPurification of 40 mg by preparative HPLC
washelution with solvents A and B (from Example 1; 95% to 5% solvent A)

Sources & evidence

ORD record: ord-d79e1ec3037c472bb32d8301e5451d75
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856326

Reaction notes

Loading…