Boc-Thr(Bzl)-Pro-OH → Boc-Thr(Bzl)-Pro-Gln-Thr(Bzl)-Asp(OBzl)-Val-Gly-Ala-Gly-Thr(Bzl)-Pro-NH2

HRID 1590987Notes

Reaction equation

HRID 1590987 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:22]([NH:24][C@H:25]([C:37]([NH:39][C@H:40]([C:44]([NH:46][CH2:47][C:48]([NH:50][C@H:51]([C:53]([NH:55][CH2:56][C:57]([NH:59][C@H:60]([C:71]([N:73]1[CH2:80][CH2:79][CH2:78][C@H:74]1[C:75]([NH2:77])=[O:76])=[O:72])[C@@H:61]([CH3:70])[O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:58])=[O:54])[CH3:52])=[O:49])=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:38])[CH2:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:23])[C@@H:12]([CH3:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[NH:88]([C:110]([O:112][C:113]([CH3:116])([CH3:115])[CH3:114])=[O:111])[C@H:89]([C:100]([N:102]1[CH2:109][CH2:108][CH2:107][C@H:103]1[C:104]([OH:106])=O)=[O:101])[C@@H:90]([CH3:99])[O:91][CH2:92][C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1>>[NH:88]([C:110]([O:112][C:113]([CH3:114])([CH3:115])[CH3:116])=[O:111])[C@H:89]([C:100]([N:102]1[CH2:109][CH2:108][CH2:107][C@H:103]1[C:104]([NH:1][C@H:2]([C:8]([NH:10][C@H:11]([C:22]([NH:24][C@H:25]([C:37]([NH:39][C@H:40]([C:44]([NH:46][CH2:47][C:48]([NH:50][C@H:51]([C:53]([NH:55][CH2:56][C:57]([NH:59][C@H:60]([C:71]([N:73]1[CH2:80][CH2:79][CH2:78][C@H:74]1[C:75]([NH2:77])=[O:76])=[O:72])[C@@H:61]([CH3:70])[O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:58])=[O:54])[CH3:52])=[O:49])=[O:45])[CH:41]([CH3:43])[CH3:42])=[O:38])[CH2:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:23])[C@@H:12]([CH3:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:106])=[O:101])[C@@H:90]([CH3:99])[O:91][CH2:92][C:93]1[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=1

Participants

3

Reactant 2

HCID 13091018Boc-Thr(Bzl)-Pro-OHHCID 15928431Boc-Gln-Thr(Bzl)-Asp(OBzl)-Val-Gly-Ala-Gly-Thr(Bzl)-Pro-NH2

Product 1

HCID 131717874Boc-Thr(Bzl)-Pro-Gln-Thr(Bzl)-Asp(OBzl)-Val-Gly-Ala-Gly-Thr(Bzl)-Pro-NH2Yield 85.4%

Procedure

By using 3.08 g of Boc-Gln-Thr(Bzl)-Asp(OBzl)-Val-Gly-Ala-Gly-Thr(Bzl)-Pro-NH2 and 1.52 g of Boc-Thr(Bzl)-Pro-OH, and the same procedure as in Reference Example 15 was repeated to obtain 3.21 g (yield: 85.4%) of the above-mentioned objective product.

Sources & evidence

ORD record
ord-fdbe1c3d08364f06bcadae005bb877fe
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

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