Dimethyl Sulfoxide → HCID 131711278, compound

HRID 1764786Notes

Reaction equation

HRID 1764786 reaction equation
[NH2:1][C@H:2]([C:13]([NH:15][C@H:16]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:55]([OH:57])=[O:56])[CH2:43][CH2:44][C:45](=[O:54])[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:40])[CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:27])[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[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:58]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[C@H:59]([C:71](ON1C(=O)CCC1=O)=[O:72])[CH2:60][C:61](=[O:70])[O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.CCN(CC)CC.CS(C)=O>CN(C=O)C>[NH:58]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[C@H:59]([C:71]([NH:1][C@H:2]([C:13]([NH:15][C@H:16]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:55]([OH:57])=[O:56])[CH2:43][CH2:44][C:45](=[O:54])[O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:40])[CH2:30][O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:27])[CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[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:72])[CH2:60][C:61](=[O:70])[O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471Triethylamine2×HCID 135177984-Benzyl 1-(2,5-dioxopyrrolidin-1-yl) N-(tert-butoxycarbonyl)-L-aspartateHCID 131711279HCID 131711279, compound

Product 1

HCID 131711278HCID 131711278, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-Thr(Bzl)-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH (54.5 g, 61.7 mmol) was treated with HCl in THF (1.5 liters; 4.1 N; 40 min) and worked up as usual to give HCl.H-Thr(Bzl)-Ser(Bzl)-Ser(Bzl)-Glu(OBzl)-OH (46.3 g, 56.6 mmol) as a white powder. It was then stirred in DMF (500 ml) with Boc-Asp(OBzl)-OSu (23.7 g, 56 mmol) at 0° for 2 hours in the presence of Et3N (16 ml). The mixture was further stirred at 25° for 15 hours during which time 7.4 ml more of Et3N was added. The produce was worked up as usual and crystallized from CH2Cl2 and petroleum ether: yield, 50.35 g (82.7%); mp 111°-113°; [α]D25 = +7.21° (c l, DMSO).

Workup

  1. additionwas added
  2. customcrystallized from CH2Cl2 and petroleum ether
  3. customyield

Sources & evidence

ORD record
ord-99442fb52aaf46d89038ed1ba0034b92
Source dataset
uspto-grants-1978_09
Patent number
US04116951

Reaction notes

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