Hydrochloric Acid → HCID 131714504, compound

HRID 1285362Notes

Reaction equation

HRID 1285362 reaction equation
[NH:1]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:2]([C:6]([N:8]1[CH2:22][CH2:21][CH2:20][C@H:9]1[C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14](O)=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].Cl.[NH2:31][C@H:32]([C:37]([NH:39][CH2:40][C:41]([NH:43][C@H:44]([C:55]([NH:57][C@H:58]([C:63]([O:65][CH3:66])=[O:64])[CH2:59][CH2:60][S:61][CH3:62])=[O:56])[CH2:45][C:46]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)=[O:42])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35].CC(O)C.O(C(C)C)C(C)C>CO.C(OCC)(=O)C>[NH:1]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[C@H:2]([C:6]([N:8]1[CH2:22][CH2:21][CH2:20][C@H:9]1[C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([NH:31][C@H:32]([C:37]([NH:39][CH2:40][C:41]([NH:43][C@H:44]([C:55]([NH:57][C@H:58]([C:63]([O:65][CH3:66])=[O:64])[CH2:59][CH2:60][S:61][CH3:62])=[O:56])[CH2:45][C:46]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)=[O:42])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13988138HCID 13988138, compoundHCID 21202047Isopropyl alcohol isopropyl etherHCID 131714505HCID 131714505, compound

Product 1

HCID 131714504HCID 131714504, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Starting from 9.10 g (22.12 mmol) of BOC-Val-Pro-Pro-OH (X) and 12.30 g (22.12 mmol of HCl.H-Leu-Gly-Trp-Met-OMe (VI) and operating as described in Step 5, but using as an eluant system ethyl acetate containing an increasing amount of methanol from 5 to 30 percent during the chromatographic purification, 16.16 g (80% yield) of compound XI were obtained from iPrOH/iPr2O: m.p. 184°-190° C. [α]D20 =-98.9° (c=1, MeOH); RfB 0.13; RfC 0.58.

Workup

  1. customduring the chromatographic purification

Sources & evidence

ORD record
ord-774e65a7351d4ca09aa0e04f914dcd67
Source dataset
uspto-grants-1986_01
Patent number
US04567162

Reaction notes

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