Triethylamine → HCID 131711186, compound

HRID 2419483Notes

Reaction equation

HRID 2419483 reaction equation
[NH:1]([C:37]([O:39]C(C)(C)C)=O)[C@H:2]([C:15]([NH:17][C@H:18]([C:34]([OH:36])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:16])[CH2:3]CC(=O)OCC1C=CC=CC=1.CCN([CH2:49][CH3:50])CC.[NH:51]([C:86]([O:88][C:89]([CH3:92])([CH3:91])[CH3:90])=[O:87])[C@H:52]([C:63]([NH:65][C@H:66]([C:76](ON1C(=O)CCC1=O)=[O:77])COCC1C=CC=CC=1)=[O:64])[C@@H:53]([CH3:62])[O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1.[CH3:93][CH2:94][O:95][C:96]([CH3:98])=[O:97]>B(F)(F)F.CCOCC.C(O)(=O)C.C(Cl)(Cl)Cl>[NH:51]([C:86]([O:88][C:89]([CH3:91])([CH3:90])[CH3:92])=[O:87])[C@H:52]([C:63]([NH:65][C@H:66]([C:37]([NH:1][C@H:2]([C:15]([NH:17][C@H:18]([C:34]([OH:36])=[O:35])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:16])[CH2:3][CH2:98][C:96](=[O:97])[O:95][CH2:94][C:93]1[CH:50]=[CH:49][CH:15]=[CH:2][CH:3]=1)=[O:39])[CH2:76][O:77][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:64])[C@@H:53]([CH3:62])[O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 131711184HCID 131711184, compoundHCID 131711185HCID 131711185, compound

Product 1

HCID 131711186HCID 131711186, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8000Boron trifluoride etherateSolvent

Conditions

Temperature
25 °C

Procedure

Compound IV (2.0 g, 3.33 mmol) was dissolved in 0.4 M BF3.OEt2 in acetic acid (16.7 ml) and stirred at 25° C. for 4 hr. The solution was evaporated to a clear oil which was solidified by treatment with dry ether and drying over KOH. This material was dissolved in DMF (25 ml) and reacted with Et3N (0.47 ml) and Boc-Thr(Bzl)-Ser(Bzl)-OSu (1.89 g, 3.33 mmol) at 0° C for 1.5 hr and 25° C for 24 hr. The pH was adjusted to 8.0 (by wet pH paper) with Et3N when necessary during the course of reaction. The reaction was worked up as described above in Example 2 to yield a crystalline product from EtOAc and petroleum ether, yield 2.5 g (78.1%); mp 111°-115° C.; [α]D25 -4.8° (c 1, CHCl3). Anal. Calcd for C52H65N5O13 (968.12): C, 64.51; H, 6.76; N, 7.23. Found: C, 64.40; H, 6.60; N, 7.11.

Workup

  1. customThe solution was evaporated to a clear oil which
  2. dry with materialdrying over KOH
  3. dissolutionThis material was dissolved in DMF (25 ml)

Sources & evidence

ORD record
ord-1538e0d1fc314f44907f6df6561a6918
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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