Allyl chloroformate → HCID 131720313, compound

HRID 2293430Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:32])[CH2:14][CH:15]([NH:24][C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl[C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35]>>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13](=[O:32])[CH2:14][CH:15]([NH:24][C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:19][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

Reactant 2

HCID 18052Allyl chloroformate

HCID 131720312HCID 131720312, compound

Product 1

HCID 131720313HCID 131720313, compoundYield 74.5%

Procedure

Following the procedure described in Example 154, treatment of L-proline, 1-[2-(3,4,5-trimethoxyphenyl)-2-oxoethyl] 2-(4-aminophenyl)ethylamide (100 mg, 0.23 mmol) with allyl chloroformate (0.036 mL, 0.34 mmol) provided 90 mg of L-proline, 1-[2-(3,4,5-trimethoxyphenyl)-2-oxoethyl] 2-(4-(N-carboalloxy)aminophenyl)ethylamide as a foam.

Sources & evidence

ORD record: ord-32dcb79b3cb944519b29e1336a85f95d
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686424

Reaction notes

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