L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl ester → Boc-Gln-Thr(Bzl)-Pro-Gln-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2

HRID 1590976Notes

Reaction equation

HRID 1590976 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([N:15]1[CH2:109][CH2:108][CH2:107][C@H:16]1[C:17]([NH:19][C@H:20]([C:26]([NH:28][C@H:29]([C:40]([NH:42][C@H:43]([C:48]([NH:50][C@H:51]([C:62]([NH:64][CH2:65][C:66]([NH:68][C@H:69]([C:79]([NH:81][CH2:82][C:83]([NH:85][C@H:86]([C:97]([N:99]1[CH2:106][CH2:105][CH2:104][C@H:100]1[C:101]([NH2:103])=[O:102])=[O:98])[C@@H:87]([CH3:96])[O:88][CH2:89][C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)=[O:84])=[O:80])[CH2:70][O:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:67])=[O:63])[C@@H:52]([CH3:61])[O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:49])[CH2:44][C:45](=[O:47])[NH2:46])=[O:41])[C@@H:30]([CH3:39])[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:27])[CH2:21][CH2:22][C:23](=[O:25])[NH2:24])=[O:18])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:117]([C:136]([O:138][C:139]([CH3:142])([CH3:141])[CH3:140])=[O:137])[C@H:118]([C:124](OC1C=CC([N+]([O-])=O)=CC=1)=[O:125])[CH2:119][CH2:120][C:121](=[O:123])[NH2:122]>>[NH:117]([C:136]([O:138][C:139]([CH3:142])([CH3:141])[CH3:140])=[O:137])[C@H:118]([C:124]([NH:1][C@H:2]([C:13]([N:15]1[CH2:109][CH2:108][CH2:107][C@H:16]1[C:17]([NH:19][C@H:20]([C:26]([NH:28][C@H:29]([C:40]([NH:42][C@H:43]([C:48]([NH:50][C@H:51]([C:62]([NH:64][CH2:65][C:66]([NH:68][C@H:69]([C:79]([NH:81][CH2:82][C:83]([NH:85][C@H:86]([C:97]([N:99]1[CH2:106][CH2:105][CH2:104][C@H:100]1[C:101]([NH2:103])=[O:102])=[O:98])[C@@H:87]([CH3:96])[O:88][CH2:89][C:90]1[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=1)=[O:84])=[O:80])[CH2:70][O:71][CH2:72][C:73]1[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=1)=[O:67])=[O:63])[C@@H:52]([CH3:61])[O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:49])[CH2:44][C:45](=[O:47])[NH2:46])=[O:41])[C@@H:30]([CH3:39])[O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:27])[CH2:21][CH2:22][C:23](=[O:25])[NH2:24])=[O:18])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:125])[CH2:119][CH2:120][C:121](=[O:123])[NH2:122]

Participants

3

Reactant 2

HCID 7017891L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl esterHCID 131717871Boc-Thr(Bzl)-Pro-Gln-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2

Product 1

HCID 131717870Boc-Gln-Thr(Bzl)-Pro-Gln-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2Yield 95.8%

Procedure

By using 2.65 g of Boc-Thr(Bzl)-Pro-Gln-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2 and 907 mg of Boc-Gln-ONp, and the same procedure as in Reference Example 18 was repeated to obtain 2.74 g (yield: 95.5%) of the above-mentioned objective product.

Sources & evidence

ORD record
ord-ca8783c8349c4305a126204db8de4502
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

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