Acetaldehyde → benzyl N-[(6S,8R)-8-(ethylamino)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamate

HRID 10988Notes

Reaction equation

HRID 10988 reaction equation
[C:1](OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(NCC4C=CC=CC=4)=CN=C3CC2)=O)=CC=1)=N)(C)(C)[CH3:2].[CH2:39]([O:46][C:47](=[O:87])[N:48]([CH2:84][CH:85]=[CH2:86])[C:49]1[C:54](=[O:55])[N:53]2[C@H:56]([C:61](=[O:83])[NH:62][CH2:63][C:64]3[CH:69]=[CH:68][C:67]([C:70]([NH:72][C:73]([O:75][CH2:76][C:77]4[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=4)=[O:74])=[NH:71])=[CH:66][CH:65]=3)[CH2:57][C@:58]([NH2:60])([CH3:59])[C:52]2=[N:51][CH:50]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH2:39]([O:46][C:47](=[O:87])[N:48]([CH2:84][CH:85]=[CH2:86])[C:49]1[C:54](=[O:55])[N:53]2[C@H:56]([C:61](=[O:83])[NH:62][CH2:63][C:64]3[CH:69]=[CH:68][C:67]([C:70]([NH:72][C:73]([O:75][CH2:76][C:77]4[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=4)=[O:74])=[NH:71])=[CH:66][CH:65]=3)[CH2:57][C@:58]([NH:60][CH2:1][CH3:2])([CH3:59])[C:52]2=[N:51][CH:50]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 145857227benzyl N-[(6S,8R)-8-amino-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamateHCID 145857234tert-butyl N-[4-[[[(6S)-3-(benzylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 145857200benzyl N-[(6S,8R)-8-(ethylamino)-8-methyl-4-oxo-6-[[4-(N-phenylmethoxycarbonylcarbamimidoyl)phenyl]methylcarbamoyl]-6,7-dihydropyrrolo[1,2-a]pyrimidin-3-yl]-N-prop-2-enylcarbamateYield 54%

Procedure

Following a procedure similar to that for the preparation of intermediate 1k, 26a (30.0 mg, 0.045 mmol), acetaldehyde (2.2 mg, 0.050 mmol) and NaBH(OAc)3 (14.4 mg, 0.068 mmol) yielded 16.9 mg (54%) of 26b. MS (ESI) 692.5 (M+H+).

Sources & evidence

ORD record
ord-79a9dac262764605b237450889acef21
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Reaction notes

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