5-Fluorouracil → 1-[6-(t-Butoxycarbonylamino)-n-hexylcarbamoyl]-5-fluorouracil

HRID 728621Notes

Reaction equation

HRID 728621 reaction equation
[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[C:10](Cl)(Cl)=[O:11].C(N(CC)CC)C.[C:21]([O:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])=[O:27])([CH3:24])([CH3:23])[CH3:22].C(C(CCC)C(NCC(NCCCCCCN)=O)=O)CC>>[C:21]([O:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:10]([N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8])=[O:11])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 5

HCID 33855-FluorouracilHCID 6371PhosgeneHCID 8471TriethylamineHCID 2733170N-BOC-1,6-diaminohexaneHCID 14997852N-[N-(2-n-propyl-n-pentanoyl)glycyl]hexamethylenediamine

Product 1

HCID 149978561-[6-(t-Butoxycarbonylamino)-n-hexylcarbamoyl]-5-fluorouracilYield 91.3%

Procedure

The reaction was carried out in the same manner as in Example 7 except for using 9.06 g (69.6 mmole) of 5-fluorouracil, 6.20 g (62.7 mmole) of phosgene, 12.68 g (125.3 mmole) of triethylamine, and 11.36 g (52.5 mmole) of N-(t-butyoxycarbonyl)hexamethylenediamine synthesized in Reference example 13 in place of N-[N-(2-n-propyl-n-pentanoyl)-glycyl]hexamethylenediamine used in Example 7. The reaction mixture was treated in the same manner as in Example 7 to give 16.06 g (Yield: 91.3%) of pale yellowish crystals. 1 g of this crystals was recrystallized from 15 ml of ethyl acetate to give 0.52 g of colorless needle crystals.

Workup

  1. additionThe reaction mixture was treated in the same manner as in Example 7

Sources & evidence

ORD record
ord-3e23a7bb7375429588abb7c54b5f2a22
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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