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Triethylamine → L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide

HRID 2293382
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HRID 2293382 반응식
[C:1]12([C:11](=[O:21])[CH2:12][N:13]3[CH2:20][CH2:19][CH2:18][C@H:14]3[C:15](O)=[O:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:37]([NH:44][C:45](=[O:51])[C@H:46]([CH:48]([CH3:50])[CH3:49])[NH2:47])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[C:1]12([C:11](=[O:21])[CH2:12][N:13]3[CH2:20][CH2:19][CH2:18][C@H:14]3[C:15]([N:44]([CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:45](=[O:51])[C@H:46]([CH:48]([CH3:50])[CH3:49])[NH2:47])=[O:16])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11063601(2S)-2-Amino-N-benzyl-3-methylbutanamideHCID 542297011-(2-adamantan-1-yl-2-oxoethyl) L-proline

생성물 1

HCID 67634856L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide수율 71.6%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Using the procedure described in Example 3, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (109.1 mg, 0.37 mmol, 1.0 eq), triethylamine (156 uL, 1.12 mmol, 3.0 eq), and THF (1.5 mL), was treated with isobutyl chloroformate (53 uL, 0.41 mL, 1.1 eq), then with L-valine benzylamide (117.5 mg, 570 umol, 1.5 eq). Workup as before provided 127 mg (71%) of L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide as a white foam.

출처 및 근거

ORD 기록
ord-e5cd1097e4f44fa2a3dfc1165ce7f1b9
출처 데이터셋
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05686424

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