Dichloromethane → HCID 131714507, compound

HRID 1285364Notes

Reaction equation

HRID 1285364 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([N:8]1[CH2:56][CH2:55][CH2:54][C@H:9]1[C:10]([N:12]1[CH2:53][CH2:52][CH2:51][C@H:13]1[C:14]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:40]([NH:42][C@H:43]([C:48]([NH2:50])=[O:49])[CH2:44][CH2:45][S:46][CH3:47])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].CO.CC(O)C.O(C(C)C)C(C)C.C(Cl)[Cl:78]>>[NH2:1][C@H:2]([C:6]([N:8]1[CH2:56][CH2:55][CH2:54][C@H:9]1[C:10]([N:12]1[CH2:53][CH2:52][CH2:51][C@H:13]1[C:14]([NH:16][C@H:17]([C:22]([NH:24][CH2:25][C:26]([NH:28][C@H:29]([C:40]([NH:42][C@H:43]([C:48]([NH2:50])=[O:49])[CH2:44][CH2:45][S:46][CH3:47])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:27])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[ClH:78]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 88645420HCID 88645420, compoundHCID 131714506HCID 131714506, compound

Product 1

HCID 131714507HCID 131714507, compoundYield 68%

Procedure

Starting from 2.45 g (2.73 mmol) of BOC-Val-Pro-Pro-Leu-Gly-Trp-Met-NH2 (XV) and operating as described in Example 1, Step 6, but using as eluant systems CH2Cl2 :MeOH:H2O=85:15:1 by volume and CH2Cl2 :MeOH:H2O=80:20:1 by volume during the chromatographic purification, 1.55 g (68% yield) of compound XVI were obtained from MeOH/iPrOH/iPr2O after desalting on Sephadex G-10 (Trade Mark): m.p. 150°-158° C.; [α]D24 =-74.8° (c=1, MeOH); RFD 0.36; E1.2 0.55 Glu.

Workup

  1. customMeOH:H2O=85:15:1 by volume and CH2Cl2 :MeOH:H2O=80:20:1 by volume during the chromatographic purification

Sources & evidence

ORD record
ord-d6fe6b116c2849d99655b83a7df1dffe
Source dataset
uspto-grants-1986_01
Patent number
US04567162

Reaction notes

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